PALMITELAIDIC 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-BQYQJAHWSA-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
Clinical pharmacology of antibiotics and other drugs in cystic fibrosis.	1988 May	3293970
Fatty acid composition in serum lipids and adipose tissue in severe obesity before and after six weeks of weight loss.	1989	2583914
Fatty acids and fibrates are potent inducers of transcription of the phosphenolpyruvate carboxykinase gene in adipocytes.	1995 Dec 1	8536680
Lipoprotein secretion by intestinal Caco-2 cells is affected differently by trans and cis unsaturated fatty acids: effect of carbon chain length and position of the double bond.	1998 Sep	9734731
Study of individual trans- and cis-16:1 isomers in cow, goat, and ewe cheese fats by gas-liquid chromatography with emphasis on the trans-delta3 isomer.	2000 Sep	11026624
A pilot study of GC/MS-based serum metabolic profiling of acute rejection in renal transplantation.	2008 Apr	18346641
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

PALMITELAIDIC ACID

Common Name

English

9-HEXADECENOIC ACID, (9E)-

Systematic Name

English

(E)-HEXADEC-9-ENOIC ACID

Systematic Name

English

TRANS-PALMITOLEIC ACID

Systematic Name

English

TRANS-9-HEXADECENOIC ACID

Systematic Name

English

PALMITOLEIC ACID, (E)-

Common Name

English

Code System Code Type Description

CHEBI

59265