(S)-(-)-pulegone
cyclohexanone, 5-methyl-2-(1-methylethylidene)-, (5S)-
 
Notes:
None found
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CAS Number: 3391-90-0Picture of molecule3D/inchi
FDA UNII: HL7Z89M60H
Nikkaji Web: J598.239A
Beilstein Number: 2040703
MDL: MFCD00142347
XlogP3-AA: 2.80 (est)
Molecular Weight: 152.23672000
Formula: C10 H16 O
NMR Predictor: Predict (works with chrome or firefox)
Category: flavor and fragrance agents
 
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Physical Properties:
Appearance: colorless clear liquid (est)
Assay: 97.00 to 100.00 % 
Food Chemicals Codex Listed: No
Specific Gravity: 0.93700 @  25.00 °C.
Refractive Index: 1.48800 @  20.00 °C.
Boiling Point: 222.00 to  223.00 °C. @ 760.00 mm Hg
Vapor Pressure: 0.093000 mmHg @ 25.00 °C. (est)
Flash Point: 185.00 °F. TCC ( 85.00 °C. )
logP (o/w): 2.556 (est)
Soluble in:
 alcohol
 water, 173.7 mg/L @ 25 °C (est)
Insoluble in:
 water
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Organoleptic Properties:
Odor Description:
minty
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
Santa Cruz Biotechnology
For experimental / research use only.
(S)-(-)-Pulegone
sds
Sigma-Aldrich: Aldrich
For experimental / research use only.
(S)-(-)-Pulegone 98%
sds
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Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 22 - Harmful if swallowed.
R 36/38 - Irritating to skin and eyes.
S 02 - Keep out of the reach of children.
S 20/21 - When using do not eat, drink or smoke.
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 37/39 - Wear suitable gloves and eye/face protection.
 
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
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
 
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Safety References:
European Food Safety Authority (EFSA) reference(s):
Flavouring Group Evaluation 57 (FGE.57)[1]: Consideration of two structurally related pulegone metabolites and one ester thereof evaluated by JECFA (55th meeting)
View page or View pdf
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EPA ACToR: Toxicology Data
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Laboratory Chemical Safety Summary : 638012
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 (5S)-5-methyl-2-propan-2-ylidenecyclohexan-1-one
Chemidplus: 0003391900
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References:
 (5S)-5-methyl-2-propan-2-ylidenecyclohexan-1-one
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 638012
Pubchem (sid): 135251209
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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
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C17623
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Export Tariff Code: 2914.29.5000
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
For Odor
No odor group found for these
 cyclopentanoneFL/FR
 eucarvone 
laevo-monomenthyl glutarateFL/FR
laevo-menthyl methyl etherFL/FR
 pinocarvoneFL/FR
 umbellulone 
aldehydic
isobutyraldehydeFL/FR
anisic
 estragoleFL/FR
balsamic
isobornyl formateFL/FR
 nonyl benzoate 
camphoreous
dextro-camphorFL/FR
 camphor tree bark oilFL/FR
 herbal ethanoneFR
 thujyl alcoholFL/FR
citrus
 ocimene quintoxideFL/FR
earthy
3-octanolFL/FR
 patchouli cyclohexanolFR
floral
 citronellal diisotridecyl acetalFR
 cyclohexyl ethyl acetateFL/FR
 cyclohexyl propanolFR
2-decalinolFR
 dihydrocarvyl acetateFL/FR
2',4'-dimethyl acetophenoneFL/FR
 earthy indaneFR
 floral methanolFR
 geranium oil chinaFL/FR
 menthadienyl formateFR
 muguet butanolFR
 ylang ylang flower oilFL/FR
 ylang ylang flower oil CO2 extractFL/FR
 ylang ylang flower oil IFL/FR
 ylang ylang flower oil IIFL/FR
 ylang ylang flower oil IIIFL/FR
fruity
3-benzyl-4-heptanoneFL/FR
2-cyclopentyl cyclopentanoneFL/FR
 lilac lactoneFL/FR
green
 geranium absoluteFL/FR
 thiogeraniolFL/FR
 artemisyl ketoneFL/FR
 barosma betulina leaf oilFL/FR
1,4-cineoleFL/FR
 costmary oil (chrysanthemum balsamita)FR
 dehydroxylinalool oxideFL/FR
isodihydrolavandulolFR
(Z)-isodihydrolavandulyl acetateFR
 herbal undecanolFR
 hyssop oilFL/FR
para-menthane-3,8-diolFL/FR
 myrtenolFL/FR
3-octyl acetateFL/FR
laevo-perillaldehydeFL/FR
 perillaldehydeFL/FR
 pine hexanolFR
D-(+)-alpha-pineneFL/FR
 piperitoneFL/FR
 rosemary absoluteFL/FR
 rosemary oil moroccoFL/FR
 sabinene hydrateFL/FR
common tansy flower oilFR
common tansy flower oil dutchFR
 viridiflorolFL/FR
licorice
sweet basil oleoresinFL/FR
mentholic
 cornmint oilFL/FR
 cornmint oil indiaFL/FR
 cornmint oil terpenelessFL/FR
laevo-mentholFL/FR
dextro-neomentholFL/FR
(±)-mentholFL/FR
dextro,laevo-mentholFL/FR
(±)-isomenthoneFL/FR
laevo-menthyl acetateFL/FR
 menthyl acetateFL/FR
 menthyl acetate racemicFL/FR
 peppermint cyclohexanoneFL/FR
dextro-piperitoneFL/FR
isopulegyl acetateFL/FR
minty
 agathosma crenulata leaf oilFL/FR
 camphene hydrate 
laevo-carveolFL/FR
 carvoneFL/FR
laevo-carvoneFL/FR
cis-carvone-5,6-oxideFL/FR
 carvyl propionateFL/FR
 cyclohexanoneFR
 dihydrocarveolFL/FR
 diosphenolFL/FR
 ethyl salicylateFL/FR
bitter fennel seed oilFR
dextro-2,8-para-menthadien-1-olFL/FR
trans-para-2,8-1-menthadienolFL/FR
trans-para-menthan-2-oneFL/FR
homomentholFL/FR
(±)-menthoneFL/FR
(-)-menthoneFL/FR
 menthoxypropane diolFL/FR
homomenthyl acetateFL/FR
2-methyl cyclohexanoneFL/FR
 methyl salicylateFL/FR
 pennyroyal oilFL/FR
 pennyroyal oil spainFL/FR
 pennyroyal oil uruguayFL/FR
 peppermint oil CO2 extractFL/FR
 peppermint oil idahoFL/FR
 peppermint oil russiaFL/FR
 peppermint oil terpenelessFL/FR
beta-phellandreneFL/FR
 piperitenoneFL/FR
laevo-piperitoneFL/FR
isopropyl tiglateFL/FR
(-)-isopulegolFL/FR
isopulegyl formateFL/FR
 spearmint absoluteFL/FR
 spearmint oil americaFL/FR
 spearmint oil terpenelessFL/FR
 tetrahydrocarvoneFL/FR
 vanillin menthoxypropane diol acetalFL/FR
 wintergreen oilFL/FR
 WS-23FL/FR
spicy
N,N-diethyl octanamideFR
laevo-verbenoneFL/FR
sulfurous
 buchu mercaptanFL/FR
 grapefruit menthaneFL/FR
thujonic
 armoise oilFR
common tansy oil canadaFR
tropical
beta-cyclocitralFL/FR
woody
para-tert-butyl cyclohexanoneFR
 patchouli ethanolFR
 patchouli hexanolFR
cis-2-pinanolFR
 
For Flavor
 
No flavor group found for these
 artemisyl ketoneFL/FR
 camphene hydrate 
laevo-carveolFL/FR
 carvoneFL/FR
 carvyl propionateFL/FR
 cyclopentanoneFL/FR
2-cyclopentyl cyclopentanoneFL/FR
2',4'-dimethyl acetophenoneFL/FR
(±)-N,N-dimethyl menthyl succinamideFL
 diosphenolFL/FR
 eucarvone 
isoheptyl acetateFL
 lilac lactoneFL/FR
 limonen-10-yl acetateFL
dextro-2,8-para-menthadien-1-olFL/FR
cis+trans-para-1(7)8-menthadien-2-yl acetateFL
trans-para-2,8-1-menthadienolFL/FR
para-menthane-3,8-diolFL/FR
3-laevo-menthoxy-2-methyl propane-1,2-diolFL
 menthoxypropane diolFL/FR
 menthyl acetate racemicFL/FR
laevo-monomenthyl glutarateFL/FR
laevo-menthyl methyl etherFL/FR
 menthyl propylene glycol carbonateFL
2-methyl cyclohexanoneFL/FR
 nonyl benzoate 
beta-phellandreneFL/FR
(Z,Z)-photocitral AFL
D-(+)-alpha-pineneFL/FR
 pinocarvoneFL/FR
 piperitenoneFL/FR
 piperitenone oxideFL
isopulegyl formateFL/FR
 umbellulone 
 vanillin menthoxypropane diol acetalFL/FR
laevo-verbenoneFL/FR
 viridiflorolFL/FR
 menthyl methyl lactateFL
 thujyl alcoholFL/FR
aldehydic
isobutyraldehydeFL/FR
alliaceous
 benzyl mercaptanFL
aromatic
laevo-perillaldehydeFL/FR
camphoreous
 camphor tree bark oilFL/FR
coffee
2-isopropyl pyrazineFL
cooling
1,4-cineoleFL/FR
dextro,laevo-mentholFL/FR
laevo-mentholFL/FR
 menthyl acetateFL/FR
homomenthyl acetateFL/FR
 sabinene hydrateFL/FR
 WS-5FL
floral
 dihydrocarvyl acetateFL/FR
 geranium oil chinaFL/FR
 ylang ylang flower oilFL/FR
 ylang ylang flower oil CO2 extractFL/FR
 ylang ylang flower oil IFL/FR
 ylang ylang flower oil IIFL/FR
 ylang ylang flower oil IIIFL/FR
fruity
3-benzyl-4-heptanoneFL/FR
green
 cyclohexyl ethyl acetateFL/FR
 dihydrocarveolFL/FR
 geranium absoluteFL/FR
 ocimene quintoxideFL/FR
3-octyl acetateFL/FR
isopropyl tiglateFL/FR
 thiogeraniolFL/FR
herbal
2-acetoxy-1,8-cineoleFL
 barosma betulina leaf oilFL/FR
 hyssop oilFL/FR
 rosemary absoluteFL/FR
 rosemary oil moroccoFL/FR
licorice
sweet basil oleoresinFL/FR
 estragoleFL/FR
meaty
2-methyl 3-(methyl thio) furanFL
medicinal
dextro-camphorFL/FR
mentholic
 cornmint oilFL/FR
 cornmint oil terpenelessFL/FR
dextro-neomentholFL/FR
(±)-mentholFL/FR
 peppermint cyclohexanoneFL/FR
minty
 agathosma crenulata leaf oilFL/FR
laevo-carvoneFL/FR
cis-carvone-5,6-oxideFL/FR
 cornmint oil indiaFL/FR
 ethyl salicylateFL/FR
trans-para-menthan-2-oneFL/FR
homomentholFL/FR
(-)-menthoneFL/FR
(±)-isomenthoneFL/FR
(±)-menthoneFL/FR
laevo-menthyl acetateFL/FR
 methyl salicylateFL/FR
 myrtenolFL/FR
 pennyroyal oilFL/FR
 pennyroyal oil spainFL/FR
 pennyroyal oil uruguayFL/FR
 peppermint oil CO2 extractFL/FR
 peppermint oil idahoFL/FR
 peppermint oil russiaFL/FR
 peppermint oil terpenelessFL/FR
 piperitoneFL/FR
laevo-piperitoneFL/FR
dextro-piperitoneFL/FR
(-)-isopulegolFL/FR
 spearmint absoluteFL/FR
 spearmint oil americaFL/FR
 spearmint oil terpenelessFL/FR
 tetrahydrocarvoneFL/FR
 wintergreen oilFL/FR
 WS-23FL/FR
musty
3-octanolFL/FR
spicy
4-methyl biphenylFL
 perillaldehydeFL/FR
sulfurous
 buchu mercaptanFL/FR
 grapefruit menthaneFL/FR
tropical
beta-cyclocitralFL/FR
woody
isobornyl formateFL/FR
 dehydroxylinalool oxideFL/FR
isopulegyl acetateFL/FR
 
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Potential Uses:
 mintFR
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Occurrence (nature, food, other): note
 found in nature
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Synonyms:
 cyclohexanone, 5-methyl-2-(1-methylethylidene)-, (5S)-
 cyclohexanone, 5-methyl-2-(1-methylethylidene)-, (S)-
(S)-(-)-p-menth-4(8)-en-3-one
(S)-p-menth-4(8)-en-3-one
(S)-para-menth-4(8)-en-3-one
(S)-5-methyl-2-(1-methyl ethylidene) cyclohexanone
(S)-5-methyl-2-(1-methylethylidene)cyclohexanone
(5S)-5-methyl-2-(2-propanyliden)cyclohexanon
(5S)-5-methyl-2-(propan-2-ylidene)cyclohexanone
(5S)-5-methyl-2-propan-2-ylidenecyclohexan-1-one
(S)-2-isopropylidene-5-methyl cyclohexanone
(S)-2-isopropylidene-5-methyl-cyclohexanone
(5S)-2-isopropylidene-5-methylcyclohexanone
(5S)-2-isopropylidéne-5-méthylcyclohexanone
(S)-2-isopropylidene-5-methylcyclohexanone
(-)-pulegone
L-pulegone
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Articles:
PubMed: Enantiospecific effect of pulegone and pulegone-derived lactones on Myzus persicae (Sulz.) settling and feeding.
PubMed: Lactones. 21. Synthesis and odoriferous properties of lactones with the p-menthane system.
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: An efficient procedure for the preparation of (E)-alpha-alkylidenecycloalkanones mediated by a CeCl(3) x 7H(2)O-NaI system. Novel methodology for the synthesis of (S)-(-)-pulegone.
PubMed: Biogenetic studies in Mentha x piperita. 2. Stereoselectivity in the bioconversion of pulegone into menthone and isomenthone.
PubMed: Transformation of a monoterpene ketone, (R)-(+)-pulegone, a potent hepatotoxin, in Mucor piriformis.
PubMed: Biosynthesis of menthofuran in Mentha x piperita: stereoselective and mechanistic studies.
PubMed: Metabolic fate of S-(-)-pulegone in rat.
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