(-)-alpha-muurolene
naphthalene, 1,2,4a,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-, (1S,4aS,8aR)-
 
Notes:
None found
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CAS Number: 10208-80-7Picture of molecule3D/inchi
FDA UNII: Search
Nikkaji Web: J188.103E
CoE Number: 11011
XlogP3-AA: 4.10 (est)
Molecular Weight: 204.35628000
Formula: C15 H24
NMR Predictor: Predict (works with chrome, Edge or firefox)
EFSA/JECFA Comments: No longer supported by Industry (DG SANCO, 2012).
Category: flavoring agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
Google Books: Search
Google Scholar: with word "volatile"Search
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Perfumer and Flavorist: Search
Google Patents: Search
US Patents: Search
EU Patents: Search
Pubchem Patents: Search
PubMed: Search
NCBI: Search
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Physical Properties:
Appearance: colorless to pale yellow clear liquid (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Specific Gravity: 0.91100 to 0.91700 @  25.00 °C.
Pounds per Gallon - (est).: 7.580 to  7.630
Refractive Index: 1.50200 to 1.50800 @  20.00 °C.
Boiling Point: 271.00 to  272.00 °C. @ 760.00 mm Hg
Vapor Pressure: 0.011000 mmHg @ 25.00 °C. (est)
Flash Point: 223.00 °F. TCC ( 106.11 °C. )
logP (o/w): 6.557 (est)
Soluble in:
 alcohol
 water, 0.06276 mg/L @ 25 °C (est)
Insoluble in:
 water
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Organoleptic Properties:
Odor Description:
at 100.00 %. 
woody
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
Chemical Sources Association
Need This Item for Flavor/Food?: You can contact the CSA
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Safety Information:
 
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: flavoring agents
Recommendation for (-)-alpha-muurolene usage levels up to:
 not for fragrance use.
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.24 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 3900 (μg/person/day)
Threshold of Concern:1800 (μg/person/day)
Structure Class: I
 
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
 average usage mg/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 7.0000035.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 5.0000025.00000
Edible ices, including sherbet and sorbet (03.0): 10.0000050.00000
Processed fruit (04.1): 7.0000035.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 10.0000050.00000
Chewing gum (05.0): --
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 5.0000025.00000
Bakery wares (07.0): 10.0000050.00000
Meat and meat products, including poultry and game (08.0): 2.0000010.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 2.0000010.00000
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 5.0000025.00000
Foodstuffs intended for particular nutritional uses (13.0): 10.0000050.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 5.0000025.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 10.0000050.00000
Ready-to-eat savouries (15.0): 20.00000100.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 5.0000025.00000
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Safety References:
European Food Safety Athority(EFSA): Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...
European Food Safety Authority (EFSA) reference(s):
Flavouring Group Evaluation 25, (FGE.25)[1] - Aliphatic and aromatic hydrocarbons from chemical group 31 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf
Flavouring Group Evaluation 78 (FGE.78)[1] - Consideration of Aliphatic and alicyclic and aromatic hydrocarbons evaluated by JECFA (63rd meeting) structurally related to aliphatic and aromatic hydrocarbons evaluated by EFSA in FGE.25 - Scientific Opinion of the Panel on Food Additives,Flavourings, Processing Aids and Materials in Contact with Food (AFC)
View page or View pdf
Scientific Opinion on Flavouring Group Evaluation 25Rev1: Aliphatic and aromatic hydrocarbons from chemical group 31
View page or View pdf
Scientific Opinion on Flavouring Group Evaluation 78, Revision 1 (FGE.78Rev1): Consideration of aliphatic and alicyclic and aromatic hydrocarbons evaluated by JECFA (63rd meeting) structurally related to aliphatic and aromatic hydrocarbons evaluated by EFSA in FGE.25Rev2
View page or View pdf
Scientific Opinion on Flavouring Group Evaluation 25, Revision 2 (FGE.25Rev2): Aliphatic and aromatic hydrocarbons from chemical group 31
View page or View pdf
Scientific opinion on Flavouring Group Evaluation 25, Revision 3 (FGE.25Rev3): Aliphatic hydrocarbons from chemical group 31
View page or View pdf
EPI System: View
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 12306047
National Institute of Allergy and Infectious Diseases: Data
 (1S,4aS,8aR)-1-isopropyl-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalene
Chemidplus: 0010208807
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References:
 (1S,4aS,8aR)-1-isopropyl-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalene
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 12306047
Pubchem (sid): 135195105
Flavornet: 10208-80-7
Pherobase: View
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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
HMDB (The Human Metabolome Database): Search
FooDB: FDB016928
Typical G.C.
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 allspice fruit
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 allspice leaf
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 allspice leaf oil
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 angelica root oil @ 0.10%
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 angelica seed oil @ 0.50%
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 anise star anise fruit
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 basil plant
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 bay laurel leaf
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 bay leaf oil @ 0.00-0.05%
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 bilberry fruit - 0.005 mg/kg
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 blood orange oil (citrus sinensis l. var. sanguinello) italy @ trace%
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 blood orange oil (citrus sinensis l. var. tarocco) italy @ trace%
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 blood orange oil italy @ 0.005%
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 calamus root oil @ 0.96%
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 cananga leaf oil @ 1.1%
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 cassinia laevis flower oil australia @ 7.70%
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 cassinia laevis leaf oil australia @ 9.60%
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 cedrela wood oil @ 1.00%
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 chamomile sweet false chamomile plant
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 cinnamomum fragrans baillon leaf oil madagascar @ 0.20%
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 citronella oil ceylon @ 0.46%
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 citronella oil china @ 0.52%
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 citronella oil java @ 0.46%
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 citronella oil zimbabwe @ 0.89%
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 clary sage oil spain @ 0.40%
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 clove fruit
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 clove leaf
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 corn leaf
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 croton cajucara benth. leaf oil brazil @ 1.20%
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 cubeb oil @ 0.62%
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 cypress oil @ trace-0.10%
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 eucalyptus globulus bicostata oil @ 0.51%
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 eucalyptus globulus maidenii f. muell oil @ 0.40%
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 eucalyptus globulus oil @ 0.18%
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 fleabane oil (conyza canadensis) @ 0.10%
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 geranium leaf oil india @ 0.89%
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 geranium petiole oil india @ 0.34%
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 geranium stem oil india @ 0.08%
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 ginger rhizome oil
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 guava fruit oil reunion @ 0.40%
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 helichrysum italicum oil america @ 0.37%
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 hinoki leaf oil @ 3.81%
Data  GC  Search Trop  Picture
 hinoki root oil @ 1.71%
Data  GC  Search Trop  Picture
 hinoki wood oil @ 5.78%
Data  GC  Search Trop  Picture
 hyptis suaveolens (l.) poit. oil mali @ 0.20-0.50%
Data  GC  Search Trop  Picture
 juniper berry oil @ 10.50%
Data  GC  Search Trop  Picture
 labdanum oil @ 0.62%
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 laurel leaf oil turkey @ trace%
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 lemon balm shoot
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 lime oil distilled mexico @ 0.03%
Data  GC  Search Trop  Picture
 mango fruit - up to 0.009 mg/kg
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 manuka var. scoparium oil new zealand @ 0.77%
Data  GC  Search Trop  Picture
 melissa oil slovak republic @ 0.14%
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 mikania cordata (burm. f.) b.l. robinson var. cordata leaf oil france @ 1.10%
Data  GC  Search Trop  Picture
 myrrhinium atropurpureum schott leaf oil brazil @ 1.10%
Data  GC  Search Trop  Picture
 nutmeg - trace amount
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 orange peel oil sweet c.p. (citrus sinensis l. var. biondo comune) blond italy @ 0.004%
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 orange peel oil sweet c.p. (citrus sinensis l. var. navelina) blond italy @ 0.005%
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 orange peel oil sweet c.p. (citrus sinensis l. var. ovale) blond italy @ 0.005%
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 orange peel oil sweet c.p. (citrus sinensis l. var. valencia late) blond italy @ 0.005%
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 orange peel oil sweet c.p. (citrus sinensis l. var. washington navel) blond italy @ 0.004%
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 oregano plant
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 oregano shoot
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 pepper tree berry oil @ 1.48%
Data  GC  Search Trop  Picture
 petitgrain combava oil @ trace%
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 phlomis fruticosa l. flower oil greece @ 0.30%
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 phoebe oil brazil @ 0.10%
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 pimenta leaf oil @ 1.76%
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 pine needle oil dwarf @ 1.87%
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 pine needle oil scotch siberia @ 0.3-1.4%
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 pinus sylvestris l. needle oil estonia @ 2.80%
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 plectranthus glandulosus hook f. leaf oil cameroon @ 0.10%
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 prangos uechtritzii boiss. et hausskn. fruit oil turkey @ 0.30%
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 protium heptaphyllum (aubl.) march leaf oil brazil @ 1.00%
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 ravintsara leaf oil @ 0.11%%
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 rose oil otto bulgaria @ 0.08%
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 rosemary leaf
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 rosemary oil CO2 extract @ 0.20%
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 rosemary oil egypt @ 0.17%
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 safflower bud
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 sage leaf oil
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 salvia lavandulifolia vahl. leaf oil @ 0.10%
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 salvia plebeia oil @ 5.19%
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 santolina oil @ 0.21%
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 savin oil (juniperus phoenicea) @ 0.40%
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 savory winter savory plant
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 snake root oil canada @ 0.10%
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 tagete oil CO2 extract @ 0.29%
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 tamarind fruit oil
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 tea green tea - 7.90 mg/kg
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 tea tree oil australia @ 0.26%
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 thyme oil red spain @ 0.04-0.07%
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 vassoura oil @ 0.90%
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 yarrow oil @ trace%
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 yarrow oil greece @ trace%
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 ylang ylang oil CO2 extract @ 0.03%
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 zanthoxylum ovalifolium l. leaf oil australia @ 0.20%
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Synonyms:
(1S,4aS,8aR)-4,7-dimethyl-1-(propan-2-yl)-1,2,4a,5,6,8a-hexahydronaphthalene
2,8-dimethylene-5-isopropyl bicyclo(4.4.0)decane
(1S- (1alpha,4aalpha, 8aalpha))- 1,2,4a,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methyl ethyl) naphthalene
(-)-a-muurolene
 naphthalene, 1,2,4a,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-, (1a,4aa,8aa)-
 naphthalene, 1,2,4a,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-, (1S,4aS,8aR)-
(1S,4aS,8aR)-1-isopropyl-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalene
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Articles:
PubMed: Population Variability of Essential Oils of Pinus heldreichii from the Scardo-Pindic Mountains O┼íljak and Gali─ica.
PubMed: Evaluation of the anti-inflammatory and antinociceptive effects of the essential oil from leaves of Xylopia laevigata in experimental models.
PubMed: Intra-population chemical polymorphism in Thymus pannonicus All. growing in Slovakia.
PubMed: Antioxidant activity of essential oil and extracts of Valeriana jatamansi roots.
PubMed: Essential oil compositions and anticholinesterase activities of two edible plants Tragopogon latifolius var. angustifolius and Lycopsis orientalis.
PubMed: Herbivory-induced plant volatiles from Oryza sativa and their influence on chemotaxis behaviour of Tibraca limbativentris stal. (Hemiptera: Pentatomidae) and egg parasitoids.
PubMed: Essential oil characterization of two Azorean Cryptomeria japonica populations and their biological evaluations.
PubMed: The seasonal variation of the chemical composition of essential oils from Porcelia macrocarpa R.E. Fries (Annonaceae) and their antimicrobial activity.
PubMed: Variability of the root essential oils of Seseli rigidum Waldst. & Kit. (Apiaceae) from different populations in Serbia.
PubMed: Comparison of volatile compounds with characteristic odor in flowers and leaves of nojigiku (Chrysanthemum japonense).
PubMed: Headspace solid-phase microextraction-gas chromatography-mass spectrometry characterization of propolis volatile compounds.
PubMed: Chemical composition and anti-Trypanosoma cruzi activity of essential oils obtained from leaves of Xylopia frutescens and X. laevigata (Annonaceae).
PubMed: Diel variation in fig volatiles across syconium development: making sense of scents.
PubMed: Chemical composition, antimicrobial and antioxidant properties of the volatile oil and methanol extract of Xenophyllum poposum.
PubMed: Antimicrobial Potential and Chemical Characterization of Serbian Liverwort (Porella arboris-vitae): SEM and TEM Observations.
PubMed: Chemical constituents and anticancer effects of the essential oil from leaves of Xylopia laevigata.
PubMed: Chemical composition and anticancer activity of essential oils of Mediterranean sage (Salvia officinalis L.) grown in different environmental conditions.
PubMed: Bioactive constituents of Homalomena aromatica essential oil and its antifungal activity against dermatophytes and yeasts.
PubMed: Distillation time alters essential oil yield, composition, and antioxidant activity of male Juniperus scopulorum trees.
PubMed: Oleaginous extract from the fruits Pterodon pubescens Benth induces antinociception in animal models of acute and chronic pain.
PubMed: Chemical composition, antimicrobial and antitumor activities of the essential oils and crude extracts of Euphorbia macrorrhiza.
PubMed: Chemical composition and antibacterial activity of essential oil from Salvia mukerjeei.
PubMed: Analysis of roasted and unroasted Pistacia terebinthus volatiles using direct thermal desorption-GCxGC-TOF/MS.
PubMed: Comparison of headspace solid-phase microextraction with conventional extraction for the analysis of the volatile components in Melia azedarach.
PubMed: Changes in volatile compound composition of Antrodia camphorata during solid state fermentation.
PubMed: Chemical composition, antioxidant and antimicrobial activity of the extracts of the flowers of the Chinese plant Chimonanthus praecox.
PubMed: Effect of some essential oils on in vitro methane emission.
PubMed: [Microscopic anatomy and volatile secondary metabolites at three stages of development of the inflorescences of Lantana camara (Verbenaceae)].
PubMed: Solid-phase microextraction (SPME) analysis of six Italian populations of Ephedra nebrodensis Tineo ex Guss. subsp. nebrodensis.
PubMed: Comparative analysis of essential oil components of two Pinus species from Taibai Mountain in China.
PubMed: Inhibitor and substrate activities of sesquiterpene olefins toward +-╬┤-cadinene-8-hydroxylase, a cytochrome P450 monooxygenase (CYP706B1).
PubMed: Essential oil composition and variability of Hypericum perforatum from wild populations of northern Turkey.
PubMed: Constituents, antileishmanial activity and toxicity profile of volatile oil from berries of Croton macrostachyus.
PubMed: [Analysis of volatile oil from Ardisia brevicaulis].
PubMed: Composition and antimicrobial activity of the leaf essential oil of Litsea kostermansii from Taiwan.
PubMed: Chemical composition and antimicrobial activity of the essential oil of Anaphalis nubigena var. monocephala.
PubMed: Diversity of sesquiterpene synthases in the basidiomycete Coprinus cinereus.
PubMed: Essential oil compositions of three Lantana species from Monteverde, Costa Rica.
PubMed: Chemical Composition and Antimicrobial Properties of Piper ovatum Vahl.
PubMed: Essential oil variability in natural populations of Picea omorika, a rare European conifer.
PubMed: Dietary derived sesquiterpenes from Phyllodesmium lizardensis.
PubMed: Silvaglins and related 2,3-secodammarane derivatives - unusual types of triterpenes from Aglaia silvestris.
PubMed: Variability of the needle essential oils of Pinus peuce from different populations in Montenegro and Serbia.
PubMed: Isolation of cDNAs and functional characterisation of two multi-product terpene synthase enzymes from sandalwood, Santalum album L.
PubMed: Composition, and anti-inflammatory and antioxidant activities of the volatile oil from the fruit peel of Garcinia brasiliensis.
PubMed: The molecular and biochemical basis for varietal variation in sesquiterpene content in melon (Cucumis melo L.) rinds.
PubMed: Germacrene D cyclization: an Ab initio investigation.
PubMed: Volatile compounds on the leaf surface of intact and regrowth tarbush (Flourensia cernua DC) canopies.
PubMed: Essential oil composition of terminal branches, cones and roots of Tetraclinis articulata from Tunisia.
PubMed: Variability of the needle essential oils of Pinus heldreichii from different populations in Montenegro and Serbia.
PubMed: Geographical traceability of West Liguria extravirgin olive oils by the analysis of volatile terpenoid hydrocarbons.
PubMed: Essential oil composition of the different parts of Eryngium bourgatii Gouan from Spain.
PubMed: Main compounds responsible for off-odour of strawberries infected by Phytophthora cactorum.
PubMed: Chemical composition and antifungal activity of essential oils from different tissues of Japanese Cedar (Cryptomeria japonica).
PubMed: Chemical composition of anther volatiles in Ranunculaceae: genera-specific profiles in Anemone, Aquilegia, Caltha, Pulsatilla, Ranunculus, and Trollius species.
PubMed: Chemical composition and larvicidal activity of the essential oils from Eupatorium betonicaeforme (D.C.) Baker (Asteraceae).
PubMed: Essential oils of the leaves of the Raukaua genus (Araliaceae).
PubMed: GC-MS analysis of essential oil of Shorea robusta bast.
PubMed: The propolis of stingless bees: terpenes from the tibia of three Frieseomelitta species.
PubMed: Composition and antimicrobial activity of the essential oil of Ballota pseudodictamnus L. Bentham.
PubMed: Chemical studies of essential oils of Juniperus oxycedrus ssp. badia.
PubMed: [New data on composition of esssential oil from inflorescence of everlasting (Helichrysum arenarium(L.) Moench.)].
PubMed: Chemical analysis and antimicrobial activity of Halimium voldii.
PubMed: Sesquiterpene, alkene, and alkane hydrocarbons in virgin olive oils of different varieties and geographical origins.
PubMed: Genetic diversity of Ocimum gratissimum L. based on volatile oil constituents, flavonoids and RAPD markers.
PubMed: Isothiocyanates in myrosinase treated herb extract of Cleome chrysantha decne. and their antimicrobial activities.
PubMed: Bioactive terpenes from the soft coral Heteroxenia sp. from Mindoro, Philippines.
PubMed: Behavioral response of femaleHelicoverpa (Heliothis)armigera HB. (Lepidoptera: Noctuidae) moths to synthetic pigeonpea (Cajanus cajan L.) kairomone.
PubMed: Sesquiterpenes in the frontal gland secretions of nasute soldier termites from New Guinea.
PubMed: Components of moribund American elm trees as attractants to elm bark beetles,Hylurgopinus rufipes andScolytus multistriatus.
PubMed: Further studies of the terpenoid content in the gorgonian Eunicea succinea: 12,13-bisepieupalmerin, a new cembranolide.
PubMed: [Sesquiterpene hydrocarbons from grapes (author's transl)].
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