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General Material Information

Preferred name myrtenol
Trivial Name (±)-Myrtenol
Short Description 2-pinen-10-ol
Formula C10 H16 O
CAS Number 515-00-4
Deleted CAS Number 111957-74-5
FEMA Number 3439
Flavis Number 2.091
ECHA Number 208-193-5
FDA UNII Search
Nikkaji Number J2.625E
MDL MFCD00001341
COE Number 10285
xLogP3-AA 1.60 (est)
NMR Predictor External link
JECFA Food Flavoring 981 myrtenol
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 515-00-4 ; MYRTENOL
Synonyms
  • bicyclo(3.1.1)hept-2-ene-2-methanol, 6,6-dimethyl-
  • bicyclo[3.1.1]hept-2-ene-2-methanol, 6,6-dimethyl-
  • 6,6-dimethyl bicyclo(3.1.1)hept-2-ene-2-methanol
  • 6,6-dimethyl(3.1.1)bicyclohept-2-en-2-methanol
  • 6,6-dimethyl-2-(hydroxymethyl)bicyclo[3.1.1]hept-2-ene
  • 6,6-dimethyl-2-hydroxymethylbicyclo(3.1.1)hept-2-ene
  • 6,6-dimethyl-2-oxymethyl bicyclo(1.1.3)hept-2-ene
  • 6,6-dimethyl-2-oxymethylbicyclo[3.1.1]hept-2-ene
  • (6,6-dimethyl-4-bicyclo[3.1.1]hept-3-enyl)methanol
  • (6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-methanol
  • 6,6-dimethylbicyclo(3.1.1)hept-2-ene-2-methanol
  • (6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methanol
  • 6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-methanol
  • 2-hydroxymethyl-6,6-dimethyl bicyclo(3.1.1)hept-2-ene
  • 2-hydroxymethyl-6,6-dimethylbicyclo(3.1.1)hept-2-ene
  • (±)- myrtenol
  • (-)- pin-2-ene-10-ol
  • 2-pinen-10-ol
  • a- pinene-10-ol
  • (6,6-dimethyl-4-bicyclo[3.1.1]hept-3-enyl)methanol
  • 2-Pinen-10-ol
  • 6,6-Dimethylbicyclo[3.1.1]hept-2-ene-2-methanol
  • 6,6-Dimethyl-2-(hydroxymethyl)bicyclo[3.1.1]hept-2-ene
  • (±)-Myrtenol
  • α-Pinene-10-ol
  • NSC 408846
  • (6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)methanol

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

(6,6-dimethyl-4-bicyclo[3.1.1]hept-3-enyl)methanol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:515-00-4
Pubchem (cid):10582
Pubchem (sid):134975904
Pherobase:View
Publications by PubMed
Antibacterial Activity of Essential Oils of Edible Spices, Ocimum canum and Xylopia aethiopica.
Anti-inflammatory and chondroprotective activity of (+)-α-pinene: structural and enantiomeric selectivity.
GABAA receptor modulation by terpenoids from Sideritis extracts.
Production of flavours and fragrances via bioreduction of (4R)-(-)-carvone and (1R)-(-)-myrtenal by non-conventional yeast whole-cells.
Growth-inhibiting effects of Paeonia lactiflora root steam distillate constituents and structurally related compounds on human intestinal bacteria.
Glycosidic inhibitors of melanogenesis from leaves of Momordica charantia.
Electrophysiological and behavioral responses of the bark beetle Dendroctonus rhizophagus to volatiles from host pines and conspecifics.
Monitoring of aglycons of yew glycosides (3,5-dimethoxyphenol, myrtenol and 1-octen-3-ol) as first indicator of yew presence.
Mutual interactions between an invasive bark beetle and its associated fungi.
Oil constituents of Artemisia nilagirica var. septentrionalis growing at different altitudes.
Chemical composition of the essential oils of Rhodiola rosea L. of three different origins.
Transition metal-substituted Dawson anions as chemo- and regio-selective oxygen transfer catalysts for H2O2 in the epoxidation of allylic alcohols.
Essential oil composition of lady's mantle (Alchemilla xanthochlora Rothm.) growing wild in Alpine pastures.
Chemical composition of the essential oils of Cyperus rotundus L. from South Africa.
Quantitative variation and biosynthesis of hindgut volatiles associated with the red turpentine beetle, Dendroctonus valens LeConte, at different attack phases.
Antimicrobial activity of the essential oil obtained from roots and chemical composition of the volatile constituents from the roots, stems, and leaves of Ballota nigra from Serbia.
Aggregation pheromone of the Qinghai spruce bark beetle, Ips nitidus eggers.
P450(BM-3)-catalyzed whole-cell biotransformation of alpha-pinene with recombinant Escherichia coli in an aqueous-organic two-phase system.
Sensitive determination of monoterpene alcohols in urine by HPLC-FLD combined with ESI-MS detection after online-solid phase extraction of the monoterpene-coumarincarbamate derivates.
Fragrance material review on myrtenol.
Synthesis of phosphatidylated-monoterpene alcohols catalyzed by phospholipase D and their antiproliferative effects on human cancer cells.
Anchoring effects in a wide binding pocket: the molecular basis of regioselectivity in engineered cytochrome P450 monooxygenase from B. megaterium.
Comparing the effect of sub-critical water extraction with conventional extraction methods on the chemical composition of Lavandula stoechas.
Attraction of the southern pine beetle, Dendroctonus frontalis, to pheromone components of the western pine beetle, Dendroctonus brevicomis (Coleoptera: Curculionidae: Scolytinae), in an allopatric zone.
Chemotypic variation of essential oils in the medicinal plant, Anemopsis californica.
Improvement of P450(BM-3) whole-cell biocatalysis by integrating heterologous cofactor regeneration combining glucose facilitator and dehydrogenase in E. coli.
25 years of natural product R&D with New South Wales agriculture.
Sedative effect of monoterpene alcohols in mice: a preliminary screening.
High individual variation in pheromone production by tree-killing bark beetles (Coleoptera: Curculionidae: Scolytinae).
Electrophysiological and behavioral responses of Ips duplicatus to aggregation pheromone in Inner Mongolia, China: amitinol as a potential pheromone component.
Intra-specific biodiversity of Italian myrtle (Myrtus communis) through chemical markers profile and biological activities of leaf methanolic extracts.
Chemoenzymatic synthesis of sacranosides a and B.
Chemical composition of the essential oil of Salvia multicaulis Vahl. var. simplicifolia Boiss. growing wild in Lebanon.
Gain and loss of fruit flavor compounds produced by wild and cultivated strawberry species.
Transformation of terpenes using a Picea abies suspension culture.
Transformation of alpha-pinene using Picea abies suspension culture.
Molecular recognition in (+)-alpha-pinene oxidation by cytochrome P450cam.
Sensitive biomonitoring of monoterpene exposure by gas chromatographic-mass spectrometric measurement of hydroxy terpenes in urine.
Pinane-Type Tridentate Reagents for Enantioselective Reactions: Reduction of Ketones and Addition of Diethylzinc to Aldehydes.
Volatile components of green walnut husks.
Characterization of the key aroma compounds in dried fruits of the West African peppertree Xylopia aethiopica (Dunal) A. Rich (Annonaceae) using aroma extract dilution analysis.
Bioactive constituents of Chinese natural medicines. IV. Rhodiolae radix. (2).: On the histamine release inhibitors from the underground part of Rhodiola sacra (Prain ex Hamet) S. H. Fu (Crassulaceae): chemical structures of rhodiocyanoside D and sacranosides A and B.
Pheromones in white pine cone beetle,Conophthorus coniperda (schwarz) (Coleoptera: Scolytidae).
Thromboxane A2 receptor antagonists. III. Synthesis and pharmacological activity of 6,6-dimethylbicyclo[3.1.1]heptane derivatives with a substituted sulfonylamino group at C-2.
Secondary attraction and field activity of beetle-produced volatiles inDendroctonus terebrans.
Defensive odor emission from larvae of two sawfly species,Pristiphora erichsonii andP. wesmaeli.
Oxygenated monoterpenes produced by yeasts, isolated fromIps typographus (Coleoptera: Scolytidae) and grown in phloem medium.
The role of mass spectrometry in medicinal plant research.
Differences in attraction to semiochemicals present in sympatric pine shoot beetles,Tomicus minor andT. piniperda.
Semiochemicals produced by western balsam bark beetle,Dryocoetes confusus Swaine (Coleoptera: Scolytidae).
Field response of spruce bark beetle,Ips typographus, to aggregation pheromone candidates.
The pharmacokinetics of the bronchosecretolytic ozothin after intravenous injection.
Quantitative variation of pheromone components in the spruce bark beetleIps typographus from different attack phases.

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
FDA Substances Added to Food (formerly EAFUS):View
CHEMBL:View
Metabolomics Database:Search
UM BBD:Search
KEGG (GenomeNet):C11938
HMDB (The Human Metabolome Database):HMDB35100
FooDB:FDB013759
Export Tariff Code:2906.19.0000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 152.23672485352
Specific gravity @ 25 °C
Pounds per Gallon 8.121 to 8.18
Refractive Index 1.49 to 1.5 @ 20 °C
Boiling Point 221 to 222°C @ 760 mm Hg
Vapor Pressure 0.018 mmHg @ 25 °C
Flash Point TCC Value 89.44 °C TCC
logP (o/w) 3.22
Solubility
alcohol Yes
water, 426.9 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Herbal
woody, pine, balsamic, sweet, minty, medicinal, camphoreous, cooling
Odor strength medium
Substantivity 52 hour(s) at 100.00 %
Luebke, William tgsc, (1996) At 100.00 %. woody pine balsam sweet mint medical
Mosciano, Gerard P&F 16, No. 4, 45, (1991) Camphoreous, woody, cooling, minty with a medicinal nuance
Flavor Type: Minty
cooling, minty, camphoreous, green, medicinal
Mosciano, Gerard P&F 16, No. 4, 45, (1991) At 50.00 ppm. Cooling, minty, camphoreous, green with a medicinal nuance
General comment Cooling mint camphor green medicinal
Useful in: mint, savory spices, fruity citrus, fruity red. Herbal, Berry, Terpenic, Fruity

Occurrences

Potential Uses

Applications
Odor purposes Balsam, Blackberry, Huckleberry, Mint, Myrtle oil replacer, Nutmeg, Pine, Raspberry, Spice, Spruce, Woody
Other purposes Fir
Cosmetic purposes Perfuming agents

Safety Information

Safety information

Preferred SDS: View
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

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
maximum skin levels for fine fragrances:
0.0140 % and are based on the assumption that the fragrance mixture is used at 20% in a consumer product (IFRA Use Level Survey).(IFRA, 2004)
Recommendation for myrtenol usage levels up to:
5.0000 % in the fragrance concentrate.
use level in formulae for use in cosmetics:
0.0130 %
Dermal Systemic Exposure in Cosmetic Products:
0.0033 mg/kg/day (IFRA, 2004)
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.10 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 0.03 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 980 (μg/person/day)
Threshold of Concern:1800 (μg/person/day)
Structure Class: I
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 8
Click here to view publication 8
average usual ppmaverage maximum ppm
baked goods: --
beverages(nonalcoholic): -10.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: -10.00000
egg products: --
fats / oils: --
fish products: --
frozen dairy: -10.00000
fruit ices: -10.00000
gelatins / puddings: -10.00000
granulated sugar: --
gravies: --
hard candy: --
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: -10.00000
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --
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): 5.0000010.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): --
Edible ices, including sherbet and sorbet (03.0): 5.0000010.00000
Processed fruit (04.1): --
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 5.0000010.00000
Chewing gum (05.3): 1.100003.10000
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 5.0000010.00000
Bakery wares (07.0): --
Meat and meat products, including poultry and game (08.0): --
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): --
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): --
Foodstuffs intended for particular nutritional uses (13.0): --
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 0.500001.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 0.500001.00000
Ready-to-eat savouries (15.0): 0.100001.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 0.100001.00000

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):

Scientific Opinion on Flavouring Group Evaluation 208 Revision 1 (FGE.208Rev1): Consideration of genotoxicity data on representatives for 10 alicyclic aldehydes with the a,ß-unsaturation in ring / side-chain and precursors from chemical subgroup 2.2 of
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 208 Revision 2 (FGE.208Rev2): Consideration of genotoxicity data on alicyclic aldehydes with a,ß-unsaturation in ring/side-chain and precursors from chemical subgroup 2.2 of FGE.19
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 73, Revision 4 (FGE.73Rev4): consideration of alicyclic alcohols, aldehydes, acids and related esters evaluated by JECFA (59th and 63rd meeting) structurally related to primary saturated or unsaturated alicyclic alcohols, aldehydes, acids and esters evaluated by EFSA in FGE.12Rev5
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 208 Revision 3 (FGE.208Rev3): consideration of genotoxicity data on alicyclic aldehydes with a,ß-unsaturation in ring/side-chain and precursors from chemical subgroup 2.2 of FGE.19
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 73, Revision 5 (FGE.73Rev5): consideration of alicyclic alcohols, aldehydes, acids and related esters evaluated by JECFA (59th, 63rd and 86th meeting) and structurally related to substances evaluated in FGE.12Rev5
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):515-00-4
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :10582
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(6,6-dimethyl-4-bicyclo[3.1.1]hept-3-enyl)methanol
Chemidplus:0000515004