AFCDB: beta-Terpineol (FDB015970)

Record Information

Version

1.0

Creation date

2010-04-08 22:12:09 UTC

Update date

2019-11-26 03:12:31 UTC

Primary ID

FDB015970

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

beta-Terpineol

Description

Flavouring ingredient Terpineol is a naturally occurring monoterpene alcohol that has been isolated from a variety of sources such as cajuput oil, pine oil, and petitgrain oil. There are three isomers, alpha-, beta-, and gamma-terpineol, the last two differing only by the location of the double bond. Terpineol is usually a mixture of these isomers with alpha-terpineol as the major constituent. beta-Terpineol is found in many foods, some of which are cardamom, nutmeg, cloves, and common thyme.

CAS Number

138-87-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.99 g/L	ALOGPS
logP	2.73	ALOGPS
logP	2.23	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	19	ChemAxon
pKa (Strongest Basic)	-1	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	47.39 m³·mol⁻¹	ChemAxon
Polarizability	18.8 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

Chemical Formula

C10H18O

IUPAC name

1-methyl-4-(prop-1-en-2-yl)cyclohexan-1-ol

InChI Identifier

InChI=1S/C10H18O/c1-8(2)9-4-6-10(3,11)7-5-9/h9,11H,1,4-7H2,2-3H3

InChI Key

RUJPNZNXGCHGID-UHFFFAOYSA-N

Isomeric SMILES

CC(=C)C1CCC(C)(O)CC1

Average Molecular Weight

154.2493

Monoisotopic Molecular Weight

154.135765198

Classification

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
Cyclohexanol
Tertiary alcohol
Cyclic alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Menthane monoterpenoids (C17517 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Extracellular

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Food and nutrition:

Flavoring agent

Biological role:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 77.87%; H 11.76%; O 10.37%	DFC
Melting Point	32.5 oC
Boiling Point	Not Available
Experimental Water Solubility	2.2 mg/mL at 15 oC	STEPHEN,H & STEPHEN,T (1963)
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-00xu-9200000000-42e0b24be7f624f54cd5	2015-03-01	View Spectrum
GC-MS	beta-Terpineol, non-derivatized, GC-MS Spectrum	splash10-006x-9100000000-1e530cbd646d0e92b81e	Spectrum
GC-MS	beta-Terpineol, non-derivatized, GC-MS Spectrum	splash10-05fu-9400000000-e5bdf4c18c222c532356	Spectrum
GC-MS	beta-Terpineol, non-derivatized, GC-MS Spectrum	splash10-006x-9100000000-1e530cbd646d0e92b81e	Spectrum
GC-MS	beta-Terpineol, non-derivatized, GC-MS Spectrum	splash10-05fu-9400000000-e5bdf4c18c222c532356	Spectrum
Predicted GC-MS	beta-Terpineol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001c-9300000000-cb9314ca71a7307b2c55	Spectrum
Predicted GC-MS	beta-Terpineol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01z3-9320000000-478884b67a441baf9067	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-0900000000-8f61d15cae2b1971e796	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-5900000000-63fbe763a78c74d44537	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-9200000000-9006b2c831fe571b547a	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-91c87400dabeb77f0a21	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-95e141cc29b1b6d974b8	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-4900000000-6dffdc4ebd36173815b7	2016-08-03	View Spectrum

NMR

Type	Description		View

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB36996

CRC / DFC (Dictionary of Food Compounds) ID

KLQ50-T:KLQ50-T

EAFUS ID

3609

Dr. Duke ID

P-MENTH-8-EN-1-OL|BETA-TERPINEOL

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

138-87-4

GoodScent ID

rw1031211

SuperScent ID

Not Available

Wikipedia ID

Terpineol

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
insectifuge	24852	Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.	DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
hepatoprotective	62868	Any compound that is able to prevent damage to the liver.	CHEBI

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
must	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
pungent	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
earthy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

beta-Terpineol (FDB015970)

Structure for FDB015970 (beta-Terpineol)