4-methyl cyclohexene
cyclohexene, 4-methyl-
 
Notes:
None found
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CAS Number: 591-47-9Picture of molecule3D/inchi
Other(deleted CASRN): 26293-22-1
ECHA EINECS - REACH Pre-Reg: 209-715-4
FDA UNII: 2N22W8H0JX
Nikkaji Web: J96.132I
Beilstein Number: 1901299
MDL: MFCD00001573
XlogP3-AA: 2.70 (est)
Molecular Weight: 96.17264000
Formula: C7 H12
NMR Predictor: Predict (works with chrome, Edge or firefox)
Category: flavor and fragrance agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Appearance: colorless clear liquid (est)
Assay: 98.00 to 100.00 % sum of isomers
Food Chemicals Codex Listed: No
Specific Gravity: 0.79000 to 0.80400 @  25.00 °C.
Pounds per Gallon - (est).: 6.574 to  6.690
Refractive Index: 1.43500 to 1.44900 @  20.00 °C.
Melting Point: -16.00 °C. @ 760.00 mm Hg
Boiling Point: 102.70 °C. @ 760.00 mm Hg
Vapor Pressure: 35.974998 mmHg @ 25.00 °C. (est)
Flash Point: 30.00 °F. TCC ( -1.10 °C. ) (est)
logP (o/w): 3.454 (est)
Shelf Life: 24.00 month(s) or longer if stored properly.
Storage: store in cool, dry place in tightly sealed containers, protected from heat and light. store under nitrogen.
Storage: store under nitrogen.
Soluble in:
 alcohol
 water, 45.39 mg/L @ 25 °C (est)
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Organoleptic Properties:
Odor Description:
at 10.00 % in dipropylene glycol. 
citrus
 
Odor and/or flavor descriptions from others (if found).
 
Bedoukian Research
METHYL CYCLOHEXENE ≥97.0% (sum of isomers), Kosher
Odor Description: A pleasant citrus odor
For use in citrus compositions.
 
 
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Cosmetic Information:
None found
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Suppliers:
Frinton Laboratories
For experimental / research use only.
4-Methylcyclohexene
Santa Cruz Biotechnology
For experimental / research use only.
4-Methyl-1-cyclohexene
Sigma-Aldrich: Aldrich
For experimental / research use only.
4-Methylcyclohexene
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Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 11 - Highly flammable.
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
R 65 - Harmful: may cause lung damage if swallowed.
S 02 - Keep out of the reach of children.
S 16 - Keep away from sources of ignition - No Smoking.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36/37/39 - Wear suitable clothing, gloves and eye/face protection.
S 62 - If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label.
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for 4-methyl cyclohexene usage levels up to:
  4.0000 % in the fragrance concentrate.
 
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Safety References:
EPI System: View
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA Substance Registry Services (TSCA): 591-47-9
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 11572
National Institute of Allergy and Infectious Diseases: Data
WISER: UN 3295
WGK Germany: 3
 4-methylcyclohexene
Chemidplus: 0000591479
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References:
 4-methylcyclohexene
NIST Chemistry WebBook: Search Inchi
Canada Domestic Sub. List: 591-47-9
Pubchem (cid): 11572
Pubchem (sid): 134977269
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
HMDB (The Human Metabolome Database): Search
Export Tariff Code: 2902.19.0000
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
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Potential Blenders and core components note
 
For Odor
No odor group found for these
green pepper 
 verbena absolute spainFL/FR
 carbitolCS
 di(propylene glycol) (mixture of isomers)CS
 dipropylene glycolCS
(Z)-8-tetradecenalFL/FR
aldehydic
 citrus carbaldehydeFR
 decanal (aldehyde C-10)FL/FR
(Z)-4-dodecenalFL/FR
 green hexanalFL/FR
 mandarine undecenalFL/FR
2-methyl undecanal (aldehyde C-12 mna)FL/FR
 octanal (aldehyde C-8)FL/FR
 TMH aldehydeFR
 tridecanalFL/FR
2-tridecenalFL/FR
 undecanalFL/FR
N-/i-undecanalFR
(Z)-8-undecenalFR
10-undecenal (aldehyde C-11 undecylenic)FL/FR
animal
 costus valerolactoneFR
anisic
para-anisyl propanalFR
balsamic
 conifer acetateFR
 fenchyl acetateFL/FR
 nonyl benzoate 
 nopolFL/FR
2-phenoxyethyl formateFR
camphoreous
 butyrophenoneFL/FR
 herbal ethanoneFR
caramellic
 geranyl crotonateFR
 mesitene lactoneFR
citrus
 acetaldehyde citronellyl methyl acetalFR
 agathis australis oil 
 aldehydic nitrileFR
 bergamot oil bergaptene reduced italyFL/FR
 bergamot oil terpenelessFL/FR
beta-bisabololFL/FR
delta-3-careneFL/FR
 cedrat peel oilFL/FR
 citralFL/FR
 citral / methyl anthranilate schiff's baseFR
 citral diethyl acetalFL/FR
 citral propylene glycol acetalFL/FR
 citronella oil ceylonFL/FR
(S)-(-)-citronellalFL/FR
 citronellal / methyl anthranilate schiff's baseFR
 citronelloneFR
 citronellyl nitrileFR
 citrus ocimenolFR
 citrus unshiu peel oilFL/FR
 curacao peel oilFL/FR
(Z)-7-decenalFR
(Z)-4-decenalFL/FR
4-decenalFL/FR
(Z)-4-decenal diethyl acetalFR
isodecyl acetateFR
 dihydromyrcenolFL/FR
 dihydromyrcenyl acetateFR
 dimethyl octenoneFR
2,4-dimethyl-3-cyclohexene-1-methanyl acetateFR
(E+Z)-4,8-dimethyl-3,7-nonadien-2-yl acetateFL/FR
 dimyrcetol (IFF)FR
 dipenteneFL/FR
 dodecane nitrileFR
2-dodecanoneFL/FR
2-ethyl-1-hexanolFL/FR
homogeranyl nitrileFR
 grapefruit indeneFR
 grapefruit nitrileFR
 grapefruit oil c.p. (citrus paradisi var. duncan) italy 
 grapefruit oil c.p. californiaFL/FR
 grapefruit oil CO2 extract (citrus paradisi macf. var. falvedo)FL/FR
 grapefruit oil terpenelessFL/FR
 grapefruit pentanolFR
2-heptanolFL/FR
 heptyl phenyl acetate 
 kauri-copal leaf oil 
 lemon hexadieneFL/FR
 lemon oil c.p. californiaFL/FR
 lemon oil c.p. furocoumarin reducedFL/FR
 lemon oil italyFL/FR
 lemon oil terpenelessFL/FR
 lemon verbena oil 
 lemongrass oilFL/FR
 lemongrass oil egyptFL/FR
 lemongrass oil moroccoFL/FR
 lime octadienalFR
 lime oil CO2 extract mexicoFL/FR
 lime oil distilled mexicoFL/FR
 lime oil distilled peruFL/FR
 lime oil expressed floridaFL/FR
 lime oil expressed terpenelessFL/FR
 lime pyranFR
dextro-limoneneFL/FR
(Z)-linalool oxide (pyranoid)FL/FR
 litsea cubeba fruit oilFL/FR
 litsea cubeba oil terpenelessFL/FR
 mandarin oil (citrus reticulata blanco var. mandarin) japanFL/FR
 mandarin oil (citrus reticulata nova var. mandarin) uruguayFL/FR
 mandarin oil (citrus reticulata var. ponkan)FL/FR
 mandarin oil avana 
 mandarin oil italyFL/FR
 marine decadienalFR
 marine nitrileFR
 melissa oil slovak republic 
2-methyl decanal (aldehyde C-11 MOA)FL/FR
 methyl heptenoneFL/FR
alpha-methylene citronellalFR
 myrcenyl acetateFL/FR
 myrmac aldehydeFR
 neroli ketoneFR
 nonanal dimethyl acetalFL/FR
 nonyl anthranilate 
(+)-nootkatoneFL/FR
 ocimene quintoxideFL/FR
 ocimenolFL/FR
 octanal glycol acetalFR
 orange fruit oilFL/FR
 orange nitrileFR
blood orange oil italyFL/FR
bitter orange peel oilFL/FR
sweet orange peel oil c.p. brazilFL/FR
sweet orange peel oil c.p. californiaFL/FR
sweet orange peel oil c.p. chinaFL/FR
sweet orange peel oil c.p. egyptFL/FR
sweet orange peel oil c.p. floridaFL/FR
sweet orange peel oil c.p. valenciaFL/FR
sweet orange peel oil distilledFL/FR
bitter orange peel oil terpenelessFL/FR
sweet orange peel oil terpenelessFL/FR
 petitgrain absolute franceFL/FR
 petitgrain bergamot oilFL/FR
 petitgrain lime oilFL/FR
alpha-sinensalFL/FR
 tangerine acetateFR
 tangerine nitrileFR
 tangerine oil americaFL/FR
 tangerine oil terpenelessFL/FR
alpha-terpinyl methyl etherFL/FR
2-tetradecenalFL/FR
(E)-2-tetradecenalFL/FR
 tetrahydrocitralFL/FR
 tetrahydromyrcenolFR
 tetrahydromyrcenyl acetateFR
 trimethyl cyclohexeneFR
(±)-2,4,8-trimethyl-7-nonen-2-olFL/FR
10-undecen-1-olFL/FR
 valenceneFL/FR
 verbena oil spainFL/FR
 verbena oil terpenelessFL/FR
 waxy nitrileFR
clean
 clean nitrileFR
coconut
 coconut decanone methylFR
delta-heptalactoneFL/FR
 tetrahydrojasmoneFR
coumarinic
 tonka bean resinoidFR
 tonka ketoneFR
earthy
3-octanolFL/FR
fatty
2,4-decadien-1-olFL/FR
 decanoic acidFL/FR
2-decen-1-olFL/FR
(E,Z)-2,6-dodecadienalFL/FR
 methyl 10-undecenoateFL/FR
(E)-2-nonenalFL/FR
10-undecen-2-oneFL/FR
floral
alpha-amyl cinnamaldehyde diethyl acetalFR
 amyl salicylateFL/FR
 autumn carboxylateFR
 bigarade oxideFR
 boronia butenalFR
 citronellalFL/FR
 citronellolFL/FR
 citronellyl acetateFL/FR
 citronellyl butyrateFL/FR
 citronellyl ethyl etherFR
 citronellyl isovalerateFL/FR
 citrus propanolFR
 cyclamen aldehyde / methyl anthranilate schiff's baseFR
 decanal / methyl anthranilate schiff's baseFR
 dihydrocitronellyl ethyl etherFR
 dihydrolinaloolFL/FR
 ethyl safranateFR
 freesia acetateFR
 gardenia acetalFR
 gardenia amideFR
 gardenia decaloneFR
 hexenyl cyclopentanoneFR
 hyacinth etherFR
 hydroxycitronellal / methyl anthranilate schiff's baseFR
 jasmin lactone (IFF)FL/FR
 leerall / methyl anthranilate schiff's baseFR
 lemon oil distilledFL/FR
 lilyall / methyl anthranilate schiff's baseFR
 magnolia indeneFR
 methoxycitronellalFR
 methoxymelonalFL/FR
 muguet carbaldehydeFR
 muguet octadienolFR
 myrcenolFL/FR
alpha-naphthyl methyl ketoneFL/FR
 nerolFL/FR
 nerolidolFL/FR
 neryl acetateFL/FR
 neryl isovalerateFL/FR
 nonanal / methyl anthranilate schiff's baseFR
 nonyl heptanoate 
 ocean propanal / methyl anthranilate schiff's baseFR
beta-ocimeneFL/FR
2-pentyl cyclopentanoneFR
 petitgrain grapefruit oilFL/FR
 petitgrain lemon oil terpenelessFL/FR
 petitgrain mandarin oil terpenelessFL/FR
 petitgrain oil paraguayFL/FR
 phenethyl pivalateFL/FR
 phenoxyethanolFL/FR
 rhodinyl acetateFL/FR
 rose carboxylateFR
 terpinyl formateFL/FR
 tetrahydroionyl acetateFR
 tetrahydrolinalyl acetateFR
(E)-2,5,9-trimethyl-4,9-decadien-1-alFR
 undecanal dimethyl acetalFR
fruity
 allyl amyl glycolateFR
 allyl benzoateFR
 allyl salicylateFR
isoamyl 2-methyl butyrateFL/FR
 apple crotonateFR
 apricot isobutyrateFR
 benzaldehyde / methyl anthranilate schiff's baseFR
 benzyl heptanoateFL/FR
 berry hexanoateFR
 bisaboleneFL/FR
 ethyl (E)-4-octenoateFR
 ethyl 2-cyclohexyl propionateFR
 ethyl 3-hydroxyhexanoateFL/FR
 ethyl 3,5,5-trimethyl hexanoateFR
 ethyl isobutyrateFL/FR
 ethyl methyl anthranilateFL/FR
 fruity carboxylateFR
 fruity cyclopentanoneFR
 green acetateFR
 heptanal cyclic ethylene acetalFR
 leather propionateFR
 linalyl valerateFL/FR
 methyl acetoacetateFL/FR
(E)-2-nonen-1-yl acetateFL/FR
 nonyl isovalerateFL/FR
 ocimen-1-yl acetateFR
 peach cyclopentanoneFR
isopropyl isobutyrateFL/FR
 prune glycidateFR
 rhubarb undecaneFR
 tropical indeneFR
(E)-2-undecenalFL/FR
green
 cilantro leaf oilFL/FR
isodecanalFL/FR
 galbanum oxyacetateFR
 galbascone (IFF)FR
 green carbaldehydeFR
 green carboxylateFR
 green heptenalFR
(Z)-3-hexen-1-yl methyl carbonateFL/FR
(Z)-3-hexen-1-yl oxyacetaldehydeFR
(Z)-3-hexenal diethyl acetalFL/FR
 ivy carbaldehydeFL/FR
2,4-ivy carbaldehydeFL/FR
3,5-ivy carbaldehydeFL/FR
3,6-ivy carbaldehydeFL/FR
 ivy dioxolaneFR
 melon heptenal propylene glycol acetalFL/FR
 octanal diethyl acetalFL/FR
 octanal dimethyl acetalFL/FR
(E)-2-octen-1-olFL/FR
 phenyl acetaldehyde diethyl acetalFL/FR
 pineapple heptadienone 10%FR
 terpinyl propionateFL/FR
 violet dienyneFR
hay
para-methyl phenoxyacetaldehydeFR
herbal
6-acetoxydihydrotheaspiraneFL/FR
 acorn acetateFR
 acorus calamus rhizome oilFR
 canarium luzonicum oilFL/FR
 cardamom liquid resinFR
 dihydroterpinyl acetateFL/FR
(E)-2-dodecenalFL/FR
cis-herbal cyclohexaneFR
 herbal heptaneFR
 herbal undecanoneFR
 linalyl acetateFL/FR
 linalyl formateFL/FR
 linalyl isovalerateFL/FR
(1S,5R)-myrtenyl acetateFL/FR
 petitgrain heptaneFR
 saffron pyranoneFR
 terpinoleneFL/FR
alpha-terpinyl acetateFL/FR
 tricyclodecenyl isobutyrateFR
marine
 marine carbonitrileFR
melon
 melon carboxaldehydeFR
 watermelon ketoneFR
naphthyl
beta-naphthyl methyl etherFL/FR
2-naphthyl phenyl ketone 
spicy
 cinnamaldehyde / methyl anthranilate schiff's baseFR
 cinnamyl nitrileFR
 dianthus ethoneFR
 ginger oleoresinFL/FR
 ginger root oil brazilFL/FR
 ginger root oil chinaFL/FR
 ginger root oil cochinFL/FR
terpenic
para-cymeneFL/FR
alpha-phellandreneFL/FR
alpha-terpineolFL/FR
tobacco
 veltonal (Bedoukian)FR
tonka
 coumarinFR
 tonka bean absoluteFR
vanilla
 heliotropyl alcoholFL/FR
 vanilla cresolFR
waxy
 decanal dimethyl acetalFL/FR
3-decanoneFL/FR
(E,E)-2,4-dodecadien-1-ol 
2-nonanolFL/FR
 tetradecanalFL/FR
(E)-2-tridecenalFL/FR
1-undecanolFL/FR
woody
alpha-farneseneFL/FR
 labdanum ethanoneFR
isolongifolene epoxideFR
 marine formateFR
 methyl vetivateFR
 sabineneFL/FR
alpha-terpineneFL/FR
 verdoxanFR
 
For Flavor
 
No flavor group found for these
6-acetoxydihydrotheaspiraneFL/FR
 agathis australis oil 
 benzyl heptanoateFL/FR
 butyrophenoneFL/FR
 cedrat peel oilFL/FR
 citral propylene glycol acetalFL/FR
(S)-(-)-citronellalFL/FR
 citronellyl isovalerateFL/FR
 citrus unshiu peel oilFL/FR
beta-cubebeneFL
 curacao peel oilFL/FR
isodecanalFL/FR
 decanal dimethyl acetalFL/FR
3-decanoneFL/FR
2,4,7-decatrienalFL
(E,E,Z)-2,4,7-decatrienalFL
4-decenalFL/FR
 dihydronootkatoneFL
 dihydroterpinyl acetateFL/FR
(E+Z)-4,8-dimethyl-3,7-nonadien-2-yl acetateFL/FR
 dipenteneFL/FR
(E,E)-2,4-dodecadien-1-ol 
(Z)-4-dodecenalFL/FR
11-dodecenoic acidFL
 epoxy-2-decenalFL
2,3-epoxydecanalFL
2,3-epoxyheptanalFL
 ethyl methyl anthranilateFL/FR
 grapefruit oil c.p. (citrus paradisi var. duncan) italy 
 heliotropyl alcoholFL/FR
 heptyl phenyl acetate 
(Z)-3-hexenal diethyl acetalFL/FR
3,5-ivy carbaldehydeFL/FR
 ivy carbaldehydeFL/FR
 jasmin lactone (IFF)FL/FR
 kauri-copal leaf oil 
 lemon verbena oil 
(Z)-linalool oxide (pyranoid)FL/FR
 linalyl formateFL/FR
 linalyl valerateFL/FR
 melissa oil slovak republic 
 melon heptenal propylene glycol acetalFL/FR
(Z+E)-mercapto-para-menthan-3-oneFL
 methyl acetoacetateFL/FR
 myrcenolFL/FR
alpha-naphthyl methyl ketoneFL/FR
2-naphthyl phenyl ketone 
 nonyl anthranilate 
 nonyl benzoate 
 nonyl heptanoate 
 nonyl isovalerateFL/FR
 nopolFL/FR
 ocimenolFL/FR
green pepper 
 phenoxyethanolFL/FR
 phenyl acetaldehyde diethyl acetalFL/FR
isopropyl isobutyrateFL/FR
alpha-sinensalFL/FR
2-tetradecenalFL/FR
(Z)-8-tetradecenalFL/FR
 tetrahydrocitralFL/FR
 thioterpenesFL
10-undecen-1-olFL/FR
 verbena absolute spainFL/FR
10-undecen-2-oneFL/FR
aldehydic
 octanal (aldehyde C-8)FL/FR
2-tridecenalFL/FR
1-undecanolFL/FR
aromatic
 amyl salicylateFL/FR
balsamic
 phenethyl pivalateFL/FR
citrus
 bergamot oil bergaptene reduced italyFL/FR
 bergamot oil terpenelessFL/FR
 bisaboleneFL/FR
beta-bisabololFL/FR
delta-3-careneFL/FR
 cilantro leaf oilFL/FR
 citralFL/FR
 citral diethyl acetalFL/FR
 citronella oil ceylonFL/FR
(Z)-4-decenalFL/FR
 dehydronootkatoneFL
 grapefruit oil c.p. californiaFL/FR
 grapefruit oil CO2 extract (citrus paradisi macf. var. falvedo)FL/FR
 grapefruit oil terpenelessFL/FR
 lemon hexadieneFL/FR
 lemon oil c.p. californiaFL/FR
 lemon oil c.p. furocoumarin reducedFL/FR
 lemon oil distilledFL/FR
 lemon oil italyFL/FR
 lemon oil terpenelessFL/FR
 lemongrass oilFL/FR
 lemongrass oil egyptFL/FR
 lemongrass oil moroccoFL/FR
 lime oil CO2 extract mexicoFL/FR
 lime oil distilled mexicoFL/FR
 lime oil distilled peruFL/FR
 lime oil expressed floridaFL/FR
 lime oil expressed terpenelessFL/FR
dextro-limoneneFL/FR
 litsea cubeba fruit oilFL/FR
 mandarin oil (citrus reticulata blanco var. mandarin) japanFL/FR
 mandarin oil (citrus reticulata nova var. mandarin) uruguayFL/FR
 mandarin oil (citrus reticulata var. ponkan)FL/FR
 mandarin oil avana 
 mandarin oil italyFL/FR
2-methyl decanal (aldehyde C-11 MOA)FL/FR
 myrcenyl acetateFL/FR
 nerolFL/FR
(+)-nootkatoneFL/FR
 orange fruit oilFL/FR
blood orange oil italyFL/FR
bitter orange peel oilFL/FR
sweet orange peel oil c.p. brazilFL/FR
sweet orange peel oil c.p. californiaFL/FR
sweet orange peel oil c.p. chinaFL/FR
sweet orange peel oil c.p. egyptFL/FR
sweet orange peel oil c.p. floridaFL/FR
sweet orange peel oil c.p. valenciaFL/FR
sweet orange peel oil distilledFL/FR
sweet orange peel oil terpenelessFL/FR
bitter orange peel oil terpenelessFL/FR
 petitgrain absolute franceFL/FR
 petitgrain bergamot oilFL/FR
 petitgrain grapefruit oilFL/FR
 petitgrain lemon oil terpenelessFL/FR
 petitgrain lime oilFL/FR
 tangerine oil americaFL/FR
 tangerine oil terpenelessFL/FR
alpha-terpineolFL/FR
(±)-2,4,8-trimethyl-7-nonen-2-olFL/FR
 valenceneFL/FR
 verbena oil spainFL/FR
 verbena oil terpenelessFL/FR
ethereal
 ethyl isobutyrateFL/FR
fatty
2,4-decadien-1-olFL/FR
(E,E)-2,4-decadienalFL
2,4-decadienalFL
(E,E)-2,4-dodecadienalFL
2-dodecanoneFL/FR
2-ethyl-1-hexanolFL/FR
(E)-2-octen-1-olFL/FR
 tetradecanalFL/FR
(E,E)-2,4-undecadienalFL
10-undecenal (aldehyde C-11 undecylenic)FL/FR
floral
 citronellalFL/FR
 citronellolFL/FR
 citronellyl acetateFL/FR
 dihydrolinaloolFL/FR
 linalyl acetateFL/FR
 neryl acetateFL/FR
 rhodinyl acetateFL/FR
isoamyl 2-methyl butyrateFL/FR
 citronellyl butyrateFL/FR
 ethyl 3-hydroxyhexanoateFL/FR
2-heptanolFL/FR
 linalyl isovalerateFL/FR
 methoxymelonalFL/FR
 neryl isovalerateFL/FR
 petitgrain mandarin oil terpenelessFL/FR
 terpinyl formateFL/FR
green
 canarium luzonicum oilFL/FR
 dihydromyrcenolFL/FR
(E,Z)-2,6-dodecadienalFL/FR
alpha-farneseneFL/FR
(E,E)-2,4-hexadienalFL
(Z)-3-hexen-1-yl methyl carbonateFL/FR
2,4-ivy carbaldehydeFL/FR
3,6-ivy carbaldehydeFL/FR
 methyl heptenoneFL/FR
 nerolidolFL/FR
(E,E)-2,6-nonadienalFL
 nonanal dimethyl acetalFL/FR
(E)-2-nonenalFL/FR
beta-ocimeneFL/FR
 ocimene quintoxideFL/FR
 octanal diethyl acetalFL/FR
 octanal dimethyl acetalFL/FR
 terpinyl propionateFL/FR
herbal
 green hexanalFL/FR
 petitgrain oil paraguayFL/FR
lactonic
delta-heptalactoneFL/FR
lemon
 litsea cubeba oil terpenelessFL/FR
musty
3-octanolFL/FR
naphthyl
beta-naphthyl methyl etherFL/FR
soapy
 decanoic acidFL/FR
spicy
 ginger oleoresinFL/FR
 ginger root oil brazilFL/FR
 ginger root oil chinaFL/FR
 ginger root oil cochinFL/FR
terpenic
para-cymeneFL/FR
alpha-phellandreneFL/FR
alpha-terpineneFL/FR
waxy
 decanal (aldehyde C-10)FL/FR
2-decen-1-olFL/FR
(E)-2-dodecenalFL/FR
 mandarine undecenalFL/FR
 methyl 10-undecenoateFL/FR
2-methyl undecanal (aldehyde C-12 mna)FL/FR
2-nonanolFL/FR
(E)-2-nonen-1-yl acetateFL/FR
(E)-2-tetradecenalFL/FR
 tridecanalFL/FR
(E)-2-tridecenalFL/FR
 undecanalFL/FR
(E)-2-undecenalFL/FR
woody
 fenchyl acetateFL/FR
(1S,5R)-myrtenyl acetateFL/FR
 sabineneFL/FR
 terpinoleneFL/FR
alpha-terpinyl acetateFL/FR
alpha-terpinyl methyl etherFL/FR
 
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Potential Uses:
 abroniaFR
 ash mountain ash berryFR
 bergamotFR
 calamus oil replacerFR
 cedratFR
 cilantroFL/FR
 citronellaFR
 citrusFR
 cologneFR
 coloniaFR
 curacaoFL
 gingerFR
 grapefruitFR
 kumquatFR
 lemonFR
 lemongrassFR
 limeFR
 litsea cubebaFL/FR
 mandarinFR
 melissa oil replacerFR
 mock orangeFR
 necterineFL
 orangeFR
 orange bitter orange peelFL/FR
 rhubarbFR
 tangerineFR
 verbenaFR
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Occurrence (nature, food, other): note
 found in nature
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Synonyms:
 cyclohexene, 4-methyl-
4-methyl-1-cyclohexene
4-methylcyclohex-1-ene
4-methylcyclohexene
1,2,3,6-tetrahydrotoluene
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Articles:
PubMed: Effects of Chemical Complexity on the Autoxidation Mechanisms of Endocyclic Alkene Ozonolysis Products: From Methylcyclohexenes toward Understanding α-Pinene.
PubMed: Screening and identification of phytotoxic volatile compounds in medicinal plants and characterizations of a selected compound, eucarvone.
PubMed: Differentiation of manuka honey from kanuka honey and from jelly bush honey using HS-SPME-GC/MS and UHPLC-PDA-MS/MS.
PubMed: Chemical characterization of Brickellia cavanillesii (Asteraceae) using gas chromatographic methods.
PubMed: Assessment of Volatile Chemical Composition of the Essential Oil of Jatropha ribifolia (Pohl) Baill by HS-SPME-GC-MS Using Different Fibers.
PubMed: [Chemical composition of essential oil from Thymus citriodorus and its toxic effect on liver cancer cells].
PubMed: Catalytic hydrogenation activity and electronic structure determination of bis(arylimidazol-2-ylidene)pyridine cobalt alkyl and hydride complexes.
PubMed: Cationic D4R zinc phosphate-anionic polyoxometalate hybrids: synthesis, spectra, structure and catalytic studies.
PubMed: Larvicidal activity of essential extract of Rosmarinus officinalis against Culex quinquefasciatus.
PubMed: Isolation of volatiles from Nigella sativa seeds using microwave-assisted extraction: effect of whole extracts on canine and murine CYP1A.
PubMed: 2,2,7,7-Tetra-methyl-1,2,3,4,5,6,7,8-octa-hydro-acridine-1,8-dione.
PubMed: Repellents and acaricides as personal protection measures in the prevention of tick-borne diseases.
PubMed: Hematopoietic modulators as potential agents for the treatment of leukemia.
PubMed: In vitro antifungal activity of Burkholderia gladioli pv. agaricicola against some phytopathogenic fungi.
PubMed: Kinetics and products of the reactions of OH radicals with cyclohexene, 1-methyl-1-cyclohexene, cis-cyclooctene, and cis-cyclodecene.
PubMed: Functionalized mesoporous silica supported copper(II) and nickel(II) catalysts for liquid phase oxidation of olefins.
PubMed: Facile carbohydrate-based stereocontrolled divergent synthesis of (+)-pericosines A and B.
PubMed: [Current contact allergens].
PubMed: Perfectly alternating copolymerization of CO2 and epichlorohydrin using cobalt(III)-based catalyst systems.
PubMed: Chirogenic [3 + 2]-photocycloaddition reactions of 2-substituted naphthoquinones with cyclic alkenes.
PubMed: Can exposure limitations for well-known contact allergens be simplified? An analysis of dose-response patch test data.
PubMed: Stereostructure reassignment and determination of the absolute configuration of pericosine D(o) by a synthetic approach.
PubMed: Regioselective alkylation of heteroaromatic compounds with 3-methyl-2-quinonyl boronic acids.
PubMed: Effectiveness of different solid-phase microextraction fibres for differentiation of selected Madeira island fruits based on their volatile metabolite profile--identification of novel compounds.
PubMed: Clean photodecomposition of 1-methyl-4-phenyl-1H-tetrazole-5(4H)-thiones to carbodiimides proceeds via a biradical.
PubMed: Ozonolysis of cyclic alkenes as surrogates for biogenic terpenes: primary ozonide formation and decomposition.
PubMed: [Analysis the chemical constituents of volatile oils in Medinilla arboricola by SPME-GC-MS].
PubMed: Chemoenzymatic synthesis of carbasugars (+)-pericosines A-C from diverse aromatic cis-dihydrodiol precursors.
PubMed: Catalytic dicyanative [4+2] cycloaddition triggered by cyanopalladation of conjugated enynes under aerobic conditions.
PubMed: (3S,4R,4aS,7aR,12bS)-3-Cyclo-propyl-meth-yl-4a,9-dihy-droxy-3-methyl-7-oxo-2,3,4,4a,5,6,7,7a-octa-hydro-1H-4,12-methano-1-benzofuro[3,2-e]isoquinolin-3-ium 2,2,2-trifluoro-acetate methanol solvate.
PubMed: rac-(1R*,2S*,3S*)-Diethyl 4-methyl-2-phenyl-6-(2-phenyl-hydrazinyl-idene)cyclo-hex-4-ene-1,3-dicarboxyl-ate.
PubMed: Specific adducts formed through a radical reaction between peptides and contact allergenic hydroperoxides.
PubMed: Four mu4-oxo-bridged copper(II) complexes: magnetic properties and catalytic applications in liquid phase partial oxidation reactions.
PubMed: Facile and efficient synthesis of naturally occurring carbasugars (+)-pericosines A and C.
PubMed: Ring strain energy in the cyclooctyl system. The effect of strain energy on [3 + 2] cycloaddition reactions with azides.
PubMed: The main chemical composition and in vitro antifungal activity of the essential oils of Ocimum basilicum Linn. var. pilosum (Willd.) Benth.
PubMed: The production of myco-diesel hydrocarbons and their derivatives by the endophytic fungus Gliocladium roseum (NRRL 50072).
PubMed: Photochemistry of imidacloprid in model systems.
PubMed: New potato micro-tuber-inducing cyclohexene compounds related to theobroxide from Lasiodiplodia theobromae.
PubMed: Oxidation of p-chlorotoluene and cyclohexene catalysed by polymer-anchored oxovanadium(IV) and copper(II) complexes of amino acid derived tridentate ligands.
PubMed: Tetrahydrobenzo- and benzofurobenzopyrones as a new class of potential photoreagents toward DNA.
PubMed: 13-cis-Beta,beta-carotene and 15-cis-beta,beta-carotene.
PubMed: Purification of carbonic anhydrase from dog erythrocytes and investigation of in vitro inhibition by various compounds.
PubMed: Methyl 2-(2-hydroxy-benzyl-ideneamino)-4,5,6,7-tetra-hydro-1-benzothio-phene-3-carboxyl-ate.
PubMed: (6aR,10aR)-6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetra-hydro-6H-benzo[c]-chromen-1-yl 4-methyl-benzene-sulfonate.
PubMed: Pericosines, antitumour metabolites from the sea hare-derived fungus Periconia byssoides. Structures and biological activities.
PubMed: Energetics of the allyl group.
PubMed: First total synthesis of antitumor natural product (+)- and (-)-pericosine A: determination of absolute stereo structure.
PubMed: Patch test results with patients' own perfumes, deodorants and shaving lotions: results of the IVDK 1998-2002.
PubMed: A skin-like cytochrome P450 cocktail activates prohaptens to contact allergenic metabolites.
PubMed: Olefin epoxidation with hydrogen peroxide catalyzed by lacunary polyoxometalate [gamma-SiW10O34H2O2]4-.
PubMed: Synthesis and biological evaluation of carboacyclic nucleosides with (Z) and (E)-9-[4,4-bis(hydroxymethyl)]-2-butenyl side chain.
PubMed: Enantioselective organocatalytic formal [3 + 3]-cycloaddition of alpha,beta-unsaturated aldehydes and application to the asymmetric synthesis of (-)-isopulegol hydrate and (-)-cubebaol.
PubMed: Synthesis, structural characterization, and catalytic performance of dititanium-substituted gamma-Keggin silicotungstate.
PubMed: Bisoxazolines with one and two sidearms: stereodirecting ligands for copper-catalysed asymmetric allylic oxidations of alkenes.
PubMed: Stereochemistry and deuterium isotope effects associated with the cyclization-rearrangements catalyzed by tobacco epiaristolochene and hyoscyamus premnaspirodiene synthases, and the chimeric CH4 hybrid cyclase.
PubMed: Electrochemical olefin epoxidation employing an iron(IV)porphyrin/trisbipyridineruthenium(III) polymer catalyst.
PubMed: A conjugated diene identified as a prohapten: contact allergenic activity and chemical reactivity of proposed epoxide metabolites.
PubMed: Photodegradation chemistry of the insecticide phosmet in lipid models and in the presence of wool wax, employing a 15N-labeled compound.
PubMed: In vitro inhibition effects of some new sulfonamide inhibitors on human carbonic anhydrase I and II.
PubMed: Terpenes from Otostegia integrifolia.
PubMed: [Chemical components of essential oils from the herb of Ligularia virgaurea].
PubMed: 16-Cyano-13alpha-(5-methyl-1,3,4-oxadiazol-2-yl)-13,16-seco-17-norandrost-5-en-3beta-yl acetate.
PubMed: The induction of gene mutations and micronuclei by oxiranes and siloranes in mammalian cells in vitro.
PubMed: Thermal activation of hydrocarbon C-H bonds initiated by a tungsten allyl complex.
PubMed: Adducts of phenoxathiin and thianthrene cation radicals with alkenes and cycloalkenes.
PubMed: In vivo studies on the metabolism of the monoterpene pulegone in humans using the metabolism of ingestion-correlated amounts (MICA) approach: explanation for the toxicity differences between (S)-(-)- and (R)-(+)-pulegone.
PubMed: X-ray crystallographic and theoretical studies of an anticonvulsant enaminone: methyl 4-(4'-bromophenyl)amino-6-methyl-2-oxocyclohex-3-en-1-oate.
PubMed: In vivo exposure of female rats to toxicants may affect oocyte quality.
PubMed: Mild, fast, and stereoselective epoxide opening by ketone enolate anions. Application to synthesis of the norlignan curculigine.
PubMed: Synthesis and anticonvulsant activity of enaminones. Part 7. Synthesis and anticonvulsant evaluation of ethyl 4-[(substituted phenyl)amino]-6-methyl-2-oxocyclohex-3-ene-1-carboxylates and their corresponding 5-methylcyclohex-2-enone derivatives.
PubMed: Relative reactivity of peracids versus dioxiranes (DMDO and TFDO) in the epoxidation of alkenes. A combined experimental and theoretical analysis.
PubMed: (-)-Axinyssene: a novel cytotoxic diterpene from a Japanese marine sponge Axinyssa sp.
PubMed: 4,5,9,10-tetrahydro-4-methyl-2-phenyl-9,10-epoxy-3H,10aH-cyclobuta[a]benzo[2,3,4-de]isoquinoline-3,5-dione.
PubMed: Mutagenic activity of structurally related oxiranes and siloranes in Salmonella typhimurium.
PubMed: Effect of P-glycoprotein on the pharmacokinetics and tissue distribution of enaminone anticonvulsants: analysis by population and physiological approaches.
PubMed: Synthesis and anticonvulsant activity of enaminones. 4. Investigations on isoxazole derivatives.
PubMed: Mono- and bisadducts from the addition of thianthrene cation radical salts to cycloalkenes and alkenes.
PubMed: Detection of a "nonaromatic" NIH shift during in vivo metabolism of the monoterpene carvone in humans.
PubMed: Kinetic characterization of enzyme inhibitors using electrospray-ionization mass spectrometry coupled with multiple reaction monitoring.
PubMed: A novel mixed dimer of a norephedrine-derived chiral lithium amide and 2-lithium-1-methylimidazole, and catalytic enantioselective deprotonation of cyclohexene oxide.
PubMed: Experimental Investigation of the Primary and Secondary Deuterium Kinetic Isotope Effects for Epoxidation of Alkenes and Ethylene with m-Chloroperoxybenzoic Acid.
PubMed: Photoinitiated catalysis in Nafion membranes containing palladium(II) meso-tetrakis(N-methyl-4-pyridyl)porphyrin and iron(III) meso-tetrakis-(2,6-dichlorophenyl)porphyrin for O2-mediated oxidations of alkenes.
PubMed: In vivo studies on the metabolism of the monoterpenes S-(+)- and R-(-)-carvone in humans using the metabolism of ingestion-correlated amounts (MICA) approach.
PubMed: Inhalation toxicity studies of the alpha,beta-unsaturated ketones: ethyl vinyl ketone.
PubMed: Thermal activation of hydrocarbon C-H bonds by tungsten alkylidene complexes.
PubMed: A short stereoselective preparation of dienamides from cyclobutene compounds. Application in the synthesis of a new cyclohexene nucleoside.
PubMed: Mechanism of the antigen formation of carvone and related alpha, beta-unsaturated ketones.
PubMed: Structure-activity relationships of phenylcyclohexene and biphenyl antitubulin compounds against plant and mammalian cells.
PubMed: A Cu(II)-mediated C-H oxygenation of sterically hindered tripyridine ligands to form triangular Cu(II)3 complexes.
PubMed: Synthesis, structure, and H2O2-dependent catalytic functions of disulfide-bridged dicopper(I) and related thioether-copper(I) and thioether-copper(II) complexes.
PubMed: Reductions with lithium in low molecular weight amines and ethylenediamine
PubMed: Blocking adenylyl cyclase inhibits olfactory generator currents induced by "IP(3)-odors".
PubMed: Enantioselective Diels-Alder approach to C-3-oxygenated angucyclinones from (SS)-2-(p-tolysulfinyl)-1,4-naphthoquinone.
PubMed: Substrate range of benzylsuccinate synthase from Azoarcus sp. strain T.
PubMed: Antiinflammatory agents: new series of N-substituted amino acids with complex pyrimidine structures endowed with antiphlogistic activity.
PubMed: beta-triketones from myrtaceae: isoleptospermone from leptospermum scoparium and papuanone from corymbia dallachiana
PubMed: Determination of pyrolysis products of smoked methamphetamine mixed with tobacco by tandem mass spectrometry.
PubMed: Odorants selectively activate distinct G protein subtypes in olfactory cilia.
PubMed: Ru(3)(CO)(12)-Catalyzed Reaction of Pyridylbenzenes with Carbon Monoxide and Olefins. Carbonylation at a C-H Bond in the Benzene Ring.
PubMed: Metalloporphyrin Peroxo Complexes of Iron(III), Manganese(III), and Titanium(IV). Comparative Studies Demonstrating That the Iron(III) Complex Is Extremely Nucleophilic.
PubMed: The biotransformation of isoprene and the two isoprene monoepoxides by human cytochrome P450 enzymes, compared to mouse and rat liver microsomes.
PubMed: Synthesis of Enantiomerically Pure Bis(hydroxymethyl)-Branched Cyclohexenyl and Cyclohexyl Purines as Potential Inhibitors of HIV.
PubMed: Isoaromatization of 4-Alkylidene-3-oxo-1- cyclohexene-1-carboxylates. Convenient Synthesis of Methyl 4-Alkyl-3-hydroxybenzoates.
PubMed: Synthesis and antimicrobial activity of some new carbazoles, indazoles, quinolines, quinazolines and naphthalenes from 3-methyl-5-phenyl-6-benzylidene-2-cyclohexene-1-one.
PubMed: The discovery and structure-activity relationships of 1,2,3,6-tetrahydro-4-phenyl-1-[(arylcyclohexenyl)alkyl]pyridines. Dopamine autoreceptor agonists and potential antipsychotic agents.
PubMed: Metabolism of tetramethrin isomers in rat. I. Identification of a sulphonic acid type of conjugate and reduced metabolites.
PubMed: Structure of 6-fluoro-1,2,3,4,7,12-hexahydro-7-methyl-12-methylene- benz[a]anthracene.
PubMed: Autoxidation of tetrazepam in tablets: prediction of degradation impurities from the oxidative behavior in solution.
PubMed: Antiviral phloroglucinols from New Zealand Kunzea species.
PubMed: [Search for antimetabolites among 5-trimethylsilyluracil nucleosides and their nonglycoside analogs].
PubMed: The structure at 198 K of (1R,5R,15R,16R)-5-isopropenyl-2-methyl- 1-[N-(trans-2-phenylcyclohexyloxycarbonyl)amino]-2-cyclohexene.
PubMed: Synthesis of affinity ligands and radioactive probes for isolation and study of myo-inositol 1,4,5-trisphosphate binding proteins.
PubMed: NTP Toxicology and Carcinogenesis Studies of d-Limonene (CAS No. 5989-27-5) in F344/N Rats and B6C3F1 Mice (Gavage Studies).
PubMed: Identification of isoprenoid-type components in human expired air: a possible shunt pathway in sterol metabolism.
PubMed: Mechanism of N-acetylpenicillamine (NAPA) potentiation of biliary excretion of methyl mercury in the rat. Influence of glutathione depletors, and metabolization of NAPA and of cysteine in relation to 1-chloro-2,4-dinitrobenzene (DNB) and bromosulphophthalein (BSP) conjugation.
PubMed: Acetohydroxyacid synthase inhibitors: N-phthalyl-L-valine anilide and related compounds.
PubMed: [Screening and detection of tetrazepam and its major metabolites].
PubMed: N-acetylpenicillamine potentiation of biliary excretion of methyl mercury: influence of glutathione depletors.
PubMed: Methyl trisporate E. A sex pheromone in Phycomyces blakesleeanus.
PubMed: (+/-)-2-Depentylperhydrohistrionicotoxin: a new probe for a regulatory site on the nicotinic acetylcholine receptor-channel.
PubMed: Biliary metabolites of all-trans-retinoic acid in the rat: isolation and identification of a novel polar metabolite.
PubMed: [Antitumor and toxic properties of retinoid C15].
PubMed: Inhibition of embryonic development in Rana pipiens by 2-methyl-3-ethyl-4-phenyl-4-cyclohexene carboxylic acid (ORF 3858).
PubMed: [Synthesis of 3-amino-4-methyl-2-pentenamide, 2-amino-1-cyclohexene-1-carboxamide and 3-amino-2,4-diphenyl-2-butenamide and synthesis of 4(3H)-pyrimidone derivatives from them].
PubMed: Studies on the effect of 2-methyl-3-ethyl-4-phenyl-delta-4-cyclohexene carboxylic acid (ORF 3858) and its p-hydroxylated metabolites on uptake of 3H-estradiol-17beta by the uterus.
PubMed: Studies on the antifertility effect and metabolism of a new, postcoital oral contraceptive, 2-methyl-3-ethyl-4-phenyl-delta-4-cyclohexene carboxylic acid, sodium salt (ORF-4463).
PubMed: [Synthesis of polycyclic compounds related to steroids. XXII. Investigation in the field of stereochemistry of polycyclic compounds monoesters of cis- and trans 1-methyl-1,2-cyclohexanedicarboxylic acids or 1-methyl-4-cyclohexene-1,2-dicarboxylic acids and their conversion].
PubMed: The action of t-butyl hypochlorite on 1-methyl-4-isopropyl-3-cyclohexene [p-menthene-(3)].
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