AFCDB: cis-beta-Ocimene (FDB001462)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:58 UTC

Update date

2020-09-17 15:32:29 UTC

Primary ID

FDB001462

Secondary Accession Numbers

FDB005921
FDB029665

Chemical Information

FooDB Name

cis-beta-Ocimene

Description

Cis-beta-Ocimene is a naturally occurring organic compound found within a variety of plants and fruits. It is formally classified as an alkatriene although it is biochemically an acyclic monoterpene as it synthesized via multiple isoprene units. Acyclic monoterpens do not contain a cycle. 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-erythritol-phosphate (MEP) pathway in plastids (PMID: 7640522). There are three known Ocimene isomers including Alpha-, cis-Beta and trans-Beta-Ocimene. Alpha-Ocimene is known as 3,7-dimethyl-1,3,7-octatriene. Beta-Ocimene is known as 3,7-dimethyl-1,3,6-octatriene. Beta-Ocimene exists in two stereoisomeric forms, cis and trans, with respect to the central double bond. The ocimenes are often found naturally as mixtures of the various forms. Ocimenes are believed to act as plant defense chemicals and have anti-fungal properties. Cis-beta-Ocimene is a neutral, very hydrophobic molecule, practically insoluble in water. It exists as a pale, colorless oil. cis-Beta-Ocimene has a warm, floral, sweet odor and has a spicy, green, metallic taste. It is found naturally in a number of plants and foods including allspice, anise, basil, bay leaf, caraway seed, celery, cinnamon, coriander, dill, fennel, grapefruit, guava, lavender, lemons, limes, mandarin oranges, papaya and parsley.

CAS Number

3338-55-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.17 g/L	ALOGPS
logP	4.3	ALOGPS
logP	3.48	ChemAxon
logS	-2.9	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	49.45 m³·mol⁻¹	ChemAxon
Polarizability	17.18 Å³	ChemAxon
Number of Rings	0	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

C10H16

IUPAC name

(3Z)-3,7-dimethylocta-1,3,6-triene

InChI Identifier

InChI=1S/C10H16/c1-5-10(4)8-6-7-9(2)3/h5,7-8H,1,6H2,2-4H3/b10-8-

InChI Key

IHPKGUQCSIINRJ-NTMALXAHSA-N

Isomeric SMILES

CC(C)=CC\C=C(\C)C=C

Average Molecular Weight

136.234

Monoisotopic Molecular Weight

136.125200512

Classification

Description

Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Acyclic monoterpenoids

Alternative Parents

Substituents

Acyclic monoterpenoid
Branched unsaturated hydrocarbon
Alkatriene
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Acyclic olefin
Hydrocarbon
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

monoterpene (CHEBI:87574 )
Acyclic monoterpenoids (LMPR0102010020 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Extracellular

Subcellular:

Biofluid and excreta:

Saliva

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 88.16%; H 11.84%	CCD
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	[neutral]?max237 (?21000) ( EtOH)	CCD
Density	Not Available
Refractive Index	n 20D 1.4877	CCD

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0006-9100000000-787f7f8b1008349f2889	2015-03-01	View Spectrum
GC-MS	cis-beta-Ocimene, non-derivatized, GC-MS Spectrum	splash10-0006-9100000000-6152f1cd6b53440c9983	Spectrum
Predicted GC-MS	cis-beta-Ocimene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-052f-9200000000-ee73cf7342b73141f4b2	Spectrum
Predicted GC-MS	cis-beta-Ocimene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-4900000000-2eaaf884de00c6502b64	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f80-9400000000-4cc164b437465a5878ea	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9000000000-7a6775225dd2fcad42fc	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-0149d94bf066009726a1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-1900000000-6c29dab24724f8b32ece	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gb9-9600000000-6b5f470455096efc86c3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-1900000000-83e72aa15e384587ebd8	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-1900000000-63f5dc5fee3a530dc16f	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9000000000-cc6cf03fdb8fe15d9ed0	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-9000000000-3629c08e44aaa74c273c	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-9000000000-6dbcb07de1e825e783ab	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fvi-9000000000-a9f21d2f141933dc84a1	2021-09-25	View Spectrum

NMR

Type	Description		View

External Links

ChemSpider ID

4478390

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

5320250

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB30088

CRC / DFC (Dictionary of Food Compounds) ID

JVH11-W:JVH10-V

EAFUS ID

Not Available

Dr. Duke ID

CIS-BETA-OCIMENE|CIS-OCIMENE|(Z)-BETA-OCIMENE

BIGG ID

Not Available

KNApSAcK ID

C00000843

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

3338-55-4

GoodScent ID

rw1010541

SuperScent ID

Not Available

Wikipedia ID

Ocimene

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

JVH10-V:JVH10-V

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti staphylococcic	33282	A substance that kills or slows the growth of bacteria.	DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
citrus	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
herb	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 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
flower	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 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
warm	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
floral	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet	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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

cis-beta-Ocimene (FDB001462)

Structure for FDB001462 (cis-beta-Ocimene)