Cannabis Compound Database: Showing Compound Card for alpha-Terpineol (CDB000558)

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Record Information

Version

1.0

Created at

2020-03-19 00:43:39 UTC

Updated at

2020-12-07 19:07:31 UTC

CannabisDB ID

CDB000558

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

alpha-Terpineol

Description

Œ±-Terpineol, also known as terpineol or p-menth-1-en-8-ol, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. p-Menthane consists of the cyclohexane ring with a methyl group and an isopropyl group at positions 1 and 4 of ring, respectively. The o- and m-menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. There are three known terpineol isomers including Œ±, Œ≤, and Œ≥-terpineol, with the last two differing only by the location of the double bond. Terpineol is usually a mixture of these isomers with Œ±-terpineol as the major constituent. Alpha-Terpineol is a very hydrophobic molecule, practically insoluble in water, but soluble in organic solvents such as methanol, ethanol and ethylacetate. Terpineol has been isolated from a variety of sources such as cajuput oil, pine oil, and petitgrain oil. Œ±-Terpineol has also been detected as a volatile component of cannabis plants (PMID: 6991645 , 26657499 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-p-Menth-1-en-8-ol	ChEBI
(1R)-alpha,alpha,4-Trimethyl-3-cyclohexene-1-methanol	ChEBI
(R)-alpha,alpha,4-Trimethylcyclohex-3-ene-1-methanol	ChEBI
(R)-alpha-Terpineol	ChEBI
(+)-alpha-Terpineol	Kegg
(1R)-a,a,4-Trimethyl-3-cyclohexene-1-methanol	Generator
(1R)-Α,α,4-trimethyl-3-cyclohexene-1-methanol	Generator
(R)-a,a,4-Trimethylcyclohex-3-ene-1-methanol	Generator
(R)-Α,α,4-trimethylcyclohex-3-ene-1-methanol	Generator
(R)-a-Terpineol	Generator
(R)-Α-terpineol	Generator
(+)-a-Terpineol	Generator
(+)-Α-terpineol	Generator
a-Terpineol	Generator
Α-terpineol	Generator
(6R)-P-Menth-1-en-8-ol	HMDB
(R)-(+)-alpha-Terpineol	HMDB
(R)-2-(4-Methyl-3-cyclohexenyl)isopropanol	HMDB
(R)-P-Menth-1-en-8-ol	HMDB
(S)-(-)-P-Menth-1-en-8-ol	HMDB
1-alpha-Terpineol	HMDB, MeSH
2-(4-Methyl-3-cyclohexen-1-yl)-2-propanol	HMDB
2-(4-Methylcyclohex-3-en-1-yl)propan-2-ol	HMDB
2-(4-Methylcyclohex-3-enyl)propan-2-ol (alpha-terpineol)	HMDB
2-[(1R)-4-Methylcyclohex-3-en-1-yl]propan-2-ol	HMDB
alpha,alpha,4-Trimethyl-3-cyclohexene-1-methanol	HMDB
alpha-Terpinenol	HMDB
alpha-Terpineole	HMDB
alpha-Terpinol	HMDB
L-alpha-Terpineol	HMDB
Lily OF valley	HMDB
Terpenol	HMDB
Terpineol	HMDB
Terpineol schlechthin	HMDB
DL-alpha-Terpineol	MeSH, HMDB
alpha-Terpineol, sodium salt	MeSH, HMDB
P-Menth-1-en-8-ol	MeSH, HMDB
D-alpha-Terpineol	MeSH, HMDB
(S)-a-Terpineol	Generator, HMDB
(S)-Α-terpineol	Generator, HMDB
alpha-Terpineol	MeSH

Chemical Formula

C₁₀H₁₈O

Average Molecular Weight

154.25

Monoisotopic Molecular Weight

154.1358

IUPAC Name

2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-2-ol

Traditional Name

(+)-α-terpineol

CAS Registry Number

7785-53-7

SMILES

CC1=CC[C@@H](CC1)C(C)(C)O

InChI Identifier

InChI=1S/C10H18O/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3/t9-/m0/s1

InChI Key

WUOACPNHFRMFPN-VIFPVBQESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Monocyclic monoterpenoid
Tertiary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

alpha-terpineol (CHEBI:300 )
Menthane monoterpenoids (C09902 )
Cyclic monoterpenes (C09902 )
Menthane monoterpenoids (LMPR0102090028 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Poaceae

Biological location:

Cell and elements:

Extracellular

Subcellular:

Biofluid and excreta:

Feces

Role

Industrial application:

Personal care products:

Perfuming agent

Food and nutrition:

Flavoring agent

Household products:

Antifungal

Pharmaceutical industry:

Anti-inflammatory

Antineoplastic agent:

Anticancer agent

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	37.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.71 mg/mL at 25 °C	Not Available
logP	2.98	LI,J & PERDUE,EM (1995)

Predicted Properties

Property	Value	Source
logP	3.17	ALOGPS
logP	2.17	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	19.4	ChemAxon
pKa (Strongest Basic)	-0.87	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	48.46 m³·mol⁻¹	ChemAxon
Polarizability	19.07 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	(S)-alpha-Terpineol, non-derivatized, GC-MS Spectrum	splash10-052f-9200000000-ae93728615d3c506a1ce	Spectrum
Predicted GC-MS	(S)-alpha-Terpineol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-9100000000-a6b151ba8e67f64241ac	Spectrum
Predicted GC-MS	(S)-alpha-Terpineol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01qi-9620000000-6c96b32bd4033639edd2	Spectrum
Predicted GC-MS	(S)-alpha-Terpineol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-0540-5900000000-cda96dbf2d059d85a3c5	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-001i-9000000000-ef81a719227e0ca1dabc	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-057l-9000000000-f219b3601875dbade6b9	2012-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-1900000000-3e8ebaa4ae0750710d12	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052k-9600000000-de13f72872a89c9b2a52	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0le9-9100000000-f6bc053d285b0f1e22f4	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-0b1926cd4fc400a61e84	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udj-3900000000-b512881ea0d1ea051199	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000b-9400000000-90c166242df69d6dee01	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-118ad26f2b30eb1cab8b	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-d2363ae8d4dbdcccda80	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f6x-9500000000-4ef1ecf90c5038ba6f9e	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-5900000000-4a5f3c6978eb2913079e	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05mn-9100000000-e7d43b2d0a8d389277d1	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9000000000-c647649541c827cabb3b	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
Alien Dawg	Detected and Quantified	0.25 mg/g dry wt	David S. Wishart,...	details
Alien Dawg (Indica dominant)	Detected and Quantified	0.29 +/- 0.03 mg/g dry wt	David S. Wishart,...	details
Crown Og	Detected and Quantified	0.6 +/- 0.1 mg/g dry wt	PMID: 28861503	details
Fortune Cookies	Detected and Quantified	0.1 +/- 0.2 mg/g dry wt	PMID: 28861503	details
Gabriola	Detected and Quantified	0.62 mg/g dry wt	David S. Wishart,...	details
Gas	Detected and Quantified	0.6 +/- 0.1 mg/g dry wt	PMID: 28861503	details
Gelato	Detected and Quantified	0.9 +/- 0.1 mg/g dry wt	PMID: 28861503	details
Island Honey	Detected and Quantified	0.19 mg/g dry wt	David S. Wishart,...	details
Miami White Kush	Detected and Quantified	0.6 +/- 0.4 mg/g dry wt	PMID: 28861503	details
Og Kush	Detected and Quantified	0.5 +/- 0.4 mg/g dry wt	PMID: 28861503	details
Quadra	Detected and Quantified	0.69 mg/g dry wt	David S. Wishart,...	details
Sensi Star	Detected and Quantified	0.37 mg/g dry wt	David S. Wishart,...	details
Sensi Star (Pure Indica)	Detected and Quantified	0.34 +/- 0.01 mg/g dry wt	David S. Wishart,...	details
Sherbert	Detected and Quantified	0.5 +/- 0.4 mg/g dry wt	PMID: 28861503	details
Skywalker Og Kush	Detected and Quantified	0.7 +/- 0.4 mg/g dry wt	PMID: 28861503	details
Superman Og Kush	Detected and Quantified	0.7 +/- 0.1 mg/g dry wt	PMID: 28861503	details
Tahoe Og Kush	Detected and Quantified	0.6 +/- 0.1 mg/g dry wt	PMID: 28861503	details
Tangerine Dream	Detected and Quantified	0.22 mg/g dry wt	David S. Wishart,...	details
Tangerine Dream (Sativa dominant)	Detected and Quantified	0.16 +/- 0.00 mg/g dry wt	David S. Wishart,...	details
Trainwreck	Detected and Quantified	0.5 +/- 0.3 mg/g dry wt	PMID: 28861503	details
Triple O	Detected and Quantified	0.6 +/- 0.1 mg/g dry wt	PMID: 28861503	details

External Links

HMDB ID

HMDB0004043

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Terpineol

METLIN ID

Not Available

PubChem Compound

442501

PDB ID

Not Available

ChEBI ID

300

References

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]

Showing Compound Card for alpha-Terpineol (CDB000558)

Structure for CDB000558 (alpha-Terpineol)