2-DECENOIC ACID, (E)-

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H18O2
Molecular Weight	170.2487
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCCC\C=C\C(O)=O

InChI

InChIKey=WXBXVVIUZANZAU-CMDGGOBGSA-N

InChI=1S/C10H18O2/c1-2-3-4-5-6-7-8-9-10(11)12/h8-9H,2-7H2,1H3,(H,11,12)/b9-8+

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20572249 | https://www.ncbi.nlm.nih.gov/pubmed/18830443 | https://www.ncbi.nlm.nih.gov/pubmed/24190238 | https://www.ncbi.nlm.nih.gov/pubmed/22606023 | https://www.ncbi.nlm.nih.gov/pubmed/20933583/

(E)-2-decenoic acid is a stereoisomer of the corresponding medium-chain fatty acid in the trans configuration. This compound excreted by the caries bacterium Streptococcus mutants and inhibits the morphological transition from yeast to hyphae, an important virulence trait, in the opportunistic fungus Candida albicans. As a component of royal jelly it exhibits estrogenic effect by activation of estrogen receptor beta. Ethyl ester of trans-2-decenoic acid exerts neurotrophin-like neurotrophic activities in animal models of stress-induced anxiety-like, cerebral infarction and spinal cord injury.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
Hyphal wall protein 1 1 Target ID: P46593 Gene ID: 3645372\|\|\|3645386 Gene Symbol: HWP1 Target Organism: Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20572249	Inhibitor 8297
Estrogen receptor beta 110 Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18830443	Activator 1430	17.0 µM [IC50]
neurotrophin signaling pathway 31 Target ID: GO:0038179 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21187649	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Candida infections 20 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20572249	Curative	Basic research	Unknown Approved Use Unknown
Anxiety 267 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24190238	Primary	Preclinical	Unknown Approved Use Unknown
Cerebral infarction 14 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22606023	Primary	Preclinical	Unknown Approved Use Unknown
Spinal cord injury 13 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20933583/	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Estrogenic activities of Fatty acids and a sterol isolated from royal jelly.	2008 Sep	18830443
2-Decenoic acid ethyl ester possesses neurotrophin-like activities to facilitate intracellular signals and increase synapse-specific proteins in neurons cultured from embryonic rat brain.	2010 Dec	21187649
Streptococcus mutans inhibits Candida albicans hyphal formation by the fatty acid signaling molecule trans-2-decenoic acid (SDSF).	2010 Jul 26	20572249
2-decenoic acid ethyl ester, a compound that elicits neurotrophin-like intracellular signals, facilitating functional recovery from cerebral infarction in mice.	2012	22606023
Anxiolytic-like effect of trans-2-decenoic acid ethyl ester in stress-induced anxiety-like model mice.	2013	24190238
Disintegration of aerobic granules induced by trans-2-decenoic acid.	2013 Jan	23186667

Patents

Sample Use Guides

In Vivo Use Guide

Starting at post-natal day 20, the female rats were injected subcutaneously with trans-2-decenoic acid 1g/kg per day

Route of Administration: Other

In Vitro Use Guide

trans-2-decenoic acid increased the rate of proliferation of MCF-7 cells at concentrations of 0.01-0.1 mM

Name

Type

Language

2-DECENOIC ACID, (E)-

Common Name

English

2-DECENOIC ACID, TRANS-

Common Name

English

(E)-2-DECENOIC ACID

Systematic Name

English

FEMA NO. 3913

Code

English

(E)-2-DECENOIC ACID [FHFI]

Common Name

English

2-DECENOIC ACID, (2E)-

Systematic Name

English

TRANS-2-DECENOIC ACID

Systematic Name

English

Classification Tree Code System Code

JECFA EVALUATION

(E)-2-DECENOIC ACID