ChemFOnt: Showing chemical card for 2-Octenoic acid (CFc000000291)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:38 UTC

Chemfont ID

CFc000000291

Molecule Identification

Common Name

2-Octenoic acid

Definition

2-Octenoic acid, also known as 2-octenoate, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. 2-Octenoic acid has 8 carbon atoms. 2-Octenoic acid is also known as an olefinic fatty acid carrying a double bond at position 2. It can exist in two isomeric forms, the cis and the trans form, with the trans or 2-E form being more abundant. 2-Octenoic acid is a relatively hydrophobic molecule with a water solubility of approximately 1 g/L. The 2E-isomer has a musty, sour, cheesy aroma and a fatty or waxy taste. 2-Octenoic acid is found in the human body and is naturally produced by hepatic microsomal oxidation of aliphatic aldehydes. 2-Octenoic acid has been detected in human urine and plasma (PMID 1883862 , 8087979 , 4086594 , 1417834 , 6480773 ). 2-Octenoic acid has also been identified as a potential pheromone excreted by the male abdominal glands of the cockroach Leucophaea maderae (PMID: 17200891 ). Outside the human body 2-Octenoic acid has been detected in coffee, cranberries, mushrooms, black tea and strawberries. It is also used as a food flavourant for baked goods and candies.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(e)-2-Octenoic acid	ChEBI
2-Octenoic acid	ChEBI
trans-alpha-Octenoic acid	ChEBI
(e)-2-Octenoate	Generator
2-Octenoate	Generator
trans-a-Octenoate	Generator
trans-a-Octenoic acid	Generator
trans-alpha-Octenoate	Generator
trans-Α-octenoate	Generator
trans-Α-octenoic acid	Generator
trans-2-Octenoate	Generator
(2E)-2-Octenoic acid	HMDB
(2E)-Oct-2-enoic acid	HMDB
trans-2-Octenoic acid	HMDB, ChEBI
(e)-Oct-2-enoate	HMDB
(e)-Oct-2-enoic acid	HMDB

Chemical Formula

C₈H₁₄O₂

Average Molecular Weight

142.1956

Monoisotopic Molecular Weight

142.099379692

IUPAC Name

(2E)-oct-2-enoic acid

Traditional Name

trans-2-octenoic acid

CAS Registry Number

1577-96-4

SMILES

CCCCC\C=C\C(O)=O

InChI Identifier

InChI=1S/C8H14O2/c1-2-3-4-5-6-7-8(9)10/h6-7H,2-5H2,1H3,(H,9,10)/b7-6+

InChI Key

CWMPPVPFLSZGCY-VOTSOKGWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

monounsaturated fatty acid (CHEBI:86544 )
medium-chain fatty acid (CHEBI:86544 )
straight-chain fatty acid (CHEBI:86544 )
olefinic fatty acid (CHEBI:86544 )
Unsaturated fatty acids (LMFA01030018 )

Functional Ontology

Not Available

Liver (HMDB: HMDB0000392)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0000392)

Endogenous

Endogenous (HMDB: HMDB0000392)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.74 g/L	ALOGPS
logP	3.01	ALOGPS
logP	2.7	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	5.25	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	5	ChemAxon
Refractivity	41.37 m³·mol⁻¹	ChemAxon
Polarizability	16.45 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

External Links

HMDB ID

HMDB0001568

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001088

KNApSAcK ID

Not Available

Chemspider ID

4445841

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6328

PubChem Compound

5282714

PDB ID

Not Available

ChEBI ID

86544

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Dupont, Georges; Dulou, Raymond; Pigerol, Charles. Kharasch reactions with 1-heptene. Synthesis of octanoic and 2-octenoic acid. Compt. rend. (1955), 240 628-9.

Showing chemical card for 2-Octenoic acid (CFc000000291)

MOL for CFc000000291 (2-Octenoic acid)

3D MOL for CFc000000291 (2-Octenoic acid)

3D SDF for CFc000000291 (2-Octenoic acid)

3D-SDF for CFc000000291 (2-Octenoic acid)

PDB for CFc000000291 (2-Octenoic acid)

3D PDB for CFc000000291 (2-Octenoic acid)

SMILES for CFc000000291 (2-Octenoic acid)

INCHI for CFc000000291 (2-Octenoic acid)

Structure for CFc000000291 (2-Octenoic acid)

3D Structure for CFc000000291 (2-Octenoic acid)