PALMITOLEIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H30O2
Molecular Weight	254.4082
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCC\C=C/CCCCCCCC(O)=O

InChI

InChIKey=SECPZKHBENQXJG-FPLPWBNLSA-N

InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h7-8H,2-6,9-15H2,1H3,(H,17,18)/b8-7-

HIDE SMILES / InChI

Description
Sources: http://www.supersmart.com/en--Essential-fatty-acids--Palmitoleic-Acid-210-mg--0668 | https://www.ncbi.nlm.nih.gov/pubmed/10602315

Palmitoleic acid, commonly known as omega-7, is a rare monounsatured fatty acid, which was generally reported to benefit the skin in promoting epithelialisation, and certain gynaecological problems (vaginal mycoses). Until now, sea buckthorn (Hippophae rhamnoides), a shrub widely found in Europe and Asia, and macadamia nuts have been the principal sources. Palmitoleic acid (PMA) has anti-inflammatory and antidiabetic activities. Palmitoleic acid is a gap junction uncoupler.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Gap junction 4 Target ID: map04540 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10602315 \| https://www.ncbi.nlm.nih.gov/pubmed/10940365	Modulator 828
Tyrosinase 41 Target ID: CHEMBL5346 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20484837	Inhibitor 8297
Microphthalmia-associated transcription factor 5 Target ID: CHEMBL1075142 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20484837	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Ulcerative colitis 123 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28185444 https://clinicaltrials.gov/ct2/show/NCT01771224	Primary	Phase I 428	Unknown Approved Use Unknown
Hypertriglyceridemia 17 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25499944	Primary	Preclinical	Unknown Approved Use Unknown
Type 2 diabetes mellitus 259 Sources: http://www.supersmart.com/en--Essential-fatty-acids--Palmitoleic-Acid-210-mg--0668	Preventing	Approved 8429	Palmitoleic Acid Approved Use A purified form of omega-7 to help combat type II diabetes, atherosclerosis and metabolic syndrome.

PubMed

Title	Date	PubMed
Fatty acids and fibrates are potent inducers of transcription of the phosphenolpyruvate carboxykinase gene in adipocytes.	1995 Dec 1	8536680
Platelet trans fatty acids in relation to angiographically assessed coronary artery disease.	1996 Feb	8645355
Unsaturated fatty acids phosphorylate and destabilize ABCA1 through a phospholipase D2 pathway.	2005 Oct 28	16118212
Antimicrobial activity of n-6, n-7 and n-9 fatty acids and their esters for oral microorganisms.	2010 Aug	20541177

Patents

Sample Use Guides

In Vivo Use Guide

A double-blind, randomized, placebo-controlled pilot study was conducted in 20 patients with UC. A dose of 720 mg/day of Cis-palmitoleic acid was orally administered during 8 weeks.

Route of Administration: Oral

In Vitro Use Guide

Endothelium-dependent responses were assessed in myometrial small arteries isolated from pregnant women, using pressure myography. Responses to bradykinin were attenuated in the presence of palmitoleic acid (50 uM).

Name

Type

Language

PALMITOLEIC ACID

Systematic Name

English

CIS-PALMITOLEIC ACID

Systematic Name

English

NSC-277452

Code

English

PALMITOLEIC ACID (CONSTITUENT OF SPIRULINA) [DSC]

Common Name

English

Palmitoleic acid [WHO-DD]

Common Name

English

16:1(N-7)

Code

English

PALMITOLEIC ACID (CONSTITUENT OF SAW PALMETTO) [DSC]

Common Name

English

ZOOMERIC ACID

Common Name

English

9-CIS-HEXADECENOIC ACID

Common Name

English

OLEOPALMITIC ACID

Common Name

English

9Z-HEXADECENOIC ACID

Common Name

English

(Z)-HEXADEC-9-ENOIC ACID

Systematic Name

English

PALMITOLEIC ACID (C16:1) (CONSTITUENT OF KRILL OIL) [DSC]

Common Name

English

9-HEXADECENOIC ACID, (9Z)-

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C68382