Showing Compound trans-Geranic acid (FDB021853)

Record Information

Version

1.0

Creation date

2011-06-01 17:20:07 UTC

Update date

2025-11-19 02:40:09 UTC

Primary ID

FDB021853

Secondary Accession Numbers

FDB014944

Chemical Information

FooDB Name

trans-Geranic acid

Description

Geranic acid, also known as 3,7-dimethylocta-2,6-dienoate or geranate, is a member of the class of compounds known as acyclic monoterpenoids. Acyclic monoterpenoids are monoterpenes that do not contain a cycle. Thus, geranic acid is considered to be a fatty acid lipid molecule. Geranic acid is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Geranic acid, or 3,7-dimethyl-2,6-octadienoic acid, is a pheromone used by some organisms. It is a double bond isomer of nerolic acid .

CAS Number

4698-08-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Geranate	Generator
3,7-Dimethyl-2,6-octadienoic acid	HMDB
3,7-Dimethylocta-2,6-dienoate	HMDB, Generator
Decaprenoic acid	HMDB
Geranic acid (6ci)	HMDB
Geranoic acid	HMDB
trans-Geranate	Generator
(2E)-3,7-Dimethyl-2,6-octadienoic acid	manual
(E)-Geranic acid	manual
2,6-Octadienoic acid, 3,7-dimethyl-, (2E)-	manual
Geranic acid a	db_source
trans-Geranic acid	manual

Predicted Properties

Property	Value	Source
Water Solubility	1.22 g/L	ALOGPS
logP	2.72	ALOGPS
logP	2.82	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	5.26	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	51.05 m³·mol⁻¹	ChemAxon
Polarizability	19.53 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H16O2

IUPAC name

3,7-dimethylocta-2,6-dienoic acid

InChI Identifier

InChI=1S/C10H16O2/c1-8(2)5-4-6-9(3)7-10(11)12/h5,7H,4,6H2,1-3H3,(H,11,12)

InChI Key

ZHYZQXUYZJNEHD-UHFFFAOYSA-N

Isomeric SMILES

CC(C)=CCCC(C)=CC(O)=O

Average Molecular Weight

168.2328

Monoisotopic Molecular Weight

168.115029756

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
Medium-chain fatty acid
Branched fatty acid
Methyl-branched fatty acid
Unsaturated fatty acid
Fatty acyl
Fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

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:

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	liquid
Physical Description	Oil	DFC
Mass Composition	C 71.39%; H 9.59%; O 19.02%	DFC
Melting Point	Not Available
Boiling Point	Bp0.02 85-87°	DFC
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	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Geranic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-066u-9300000000-0e5fa74a29642ffbea56	Spectrum
Predicted GC-MS	Geranic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0600-9510000000-c63599768f78d24aff89	Spectrum
Predicted GC-MS	Geranic acid, 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	splash10-0udi-0900000000-63a39683f1ee7ae411e1	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-4900000000-69961fd8b0ac30801f92	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-066r-9000000000-5e0e3fc6d4f6195196b4	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01b9-0900000000-2ca07626a0a6f2fc98fd	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00xs-0900000000-f4de03fb18a11ded1779	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ab9-5900000000-140a8e79b9546d577420	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-d34b67d515962ee44c5f	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-e27ed5f74c7dd38be01b	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0560-9400000000-4dadcf2bbe6fc51045cd	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-9600000000-9f52332988cf28bfa12f	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00lr-9000000000-29159b17a0fa9f011058	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-067l-9000000000-5dbb614d4e9125fa59e6	2021-09-24	View Spectrum