(-)-myrtenol

General Material Information

Preferred name	(-)-myrtenol
Trivial Name	(-)-Myrtenol
Short Description	bicyclo[3.1.1]hept-2-ene-2-methanol, 6,6-dimethyl-, (1R,5S)-
Formula	C10 H16 O
CAS Number	19894-97-4
ECHA Number	243-409-1
FDA UNII	S1B8392IQY
Nikkaji Number	J15.938G
Beilstein Number	2206583
MDL	MFCD00001341
xLogP3-AA	1.60 (est)
NMR Predictor	External link
Synonyms	bicyclo[3.1.1]hept-2-ene-2-methanol, 6,6-dimethyl-, (1R,5S)- (1R)-6,6-dimethyl bicyclo(3.1.1)hept-2-ene-2-methanol (1R)-6,6-dimethylbicyclo(3.1.1)hept-2-ene-2-methanol [(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methanol (1R)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-methanol (1R)-(-)- myrtenol (R)- myrtenol (1R,5S)-2-pinen-10-ol [(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methanol 2-Pinen-10-ol, (1R,5S)-(-)- Bicyclo[3.1.1]hept-2-ene-2-methanol, 6,6-dimethyl-, (1R)- (1R,5S)-6,6-Dimethylbicyclo[3.1.1]hept-2-ene-2-methanol l-Myrtenol (1R)-(-)-Myrtenol (1R)-Myrthenol (1R,5S)-Myrtenol ((1R,5S)-6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)methanol

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Literature & References

	[(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methanol
NIST Chemistry WebBook:	Search Inchi
Pubchem (cid):	636475
Pubchem (sid):	135046875

Publications by PubMed
Terpenols as substituents for the diastereoselective formation of enantiomerically pure triple lithium-bridged helicate type-coordination compounds.
Chemical composition and antifungal activity of supercritical extract and essential oil of Tanacetum vulgare growing wild in Lithuania.
Anxiolytic-like effects and mechanism of (-)-myrtenol: a monoterpene alcohol.
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.
GABA(A) 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
UM BBD:	Search
HMDB (The Human Metabolome Database):	Search
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View
Wikipedia:	View

Suppliers

BOC Sciences	ExtraSynthese
Penta International	Sigma-Aldrich: Aldrich
Penta International Corporation

PhysChem Properties

Material listed in food chemical codex	No
Molecular weight	152.23672485352
Vapor Pressure	0.018 mmHg @ 25 °C
Flash Point TCC Value	89.4 °C TCC
logP (o/w)	2.845 est
Solubility
alcohol	Yes
water, 426.9 mg/L @ 25 °C (est)	Yes
water	No

Organoleptic Properties

Odor Type: Woody
woody, pine, balsamic, minty, medicinal
Luebke, William tgsc, (2016)	At 100.00 %. woody pine balsam sweet mint medical
Flavor Type: Minty
fir needle, camphoreous, minty, woody
Luebke, William tgsc, (2016)	Fir needle camphoreous minty woody

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:
natural substances and extractives
Recommendation for (-)-myrtenol usage levels up to:
	not for fragrance use.

Recommendation for (-)-myrtenol flavor usage levels up to:
	not for flavor use.

Safety references

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 :636475

National Institute of Allergy and Infectious Diseases:Data

WGK Germany:3

[(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methanol

Chemidplus:0019894974