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Details

Stereochemistry ACHIRAL
Molecular Formula C16H29O2.Na
Molecular Weight 276.39
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of SODIUM PALMITOLEATE

SMILES

[Na+].CCCCCC\C=C/CCCCCCCC([O-])=O

InChI

InChIKey=AQADNICIQOBXGR-CFYXSCKTSA-M
InChI=1S/C16H30O2.Na/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);/q;+1/p-1/b8-7-;

HIDE SMILES / InChI

Molecular Formula C16H29O2
Molecular Weight 253.4003
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Curator's Comment: Palmitoleic acid (16 carbon atoms) was noticed first in 1854 by Hofstädter P.G. in sperm whale oil and named physetoleic acid. In 1906 Bull H. discovered its molecular composition, at the time when Lewkowitsch gave the present name. The structure was established in 1925 by Armstrong E.F. et al.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Preventing
Palmitoleic Acid

Approved Use

A purified form of omega-7 to help combat type II diabetes, atherosclerosis and metabolic syndrome.
PubMed

PubMed

TitleDatePubMed
Platelet trans fatty acids in relation to angiographically assessed coronary artery disease.
1996 Feb
Determination of free fatty acids in human bile by high-performance liquid chromatography.
1998 Mar
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
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
Selective mobilisation of fatty acids from human adipose tissue.
2001 Apr
Beneficial effect of oleoylated lipids on paraoxonase 1: protection against oxidative inactivation and stabilization.
2003 Oct 15
Unsaturated fatty acids induce calcium influx into keratinocytes and cause abnormal differentiation of epidermis.
2005 May
Patents

Sample Use Guides

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
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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:30:05 GMT 2023
Edited
by admin
on Fri Dec 15 18:30:05 GMT 2023
Record UNII
9KXN90LI9Y
Record Status Validated (UNII)
Record Version
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Name Type Language
SODIUM PALMITOLEATE
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID901016441
Created by admin on Fri Dec 15 18:30:05 GMT 2023 , Edited by admin on Fri Dec 15 18:30:05 GMT 2023
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FDA UNII
9KXN90LI9Y
Created by admin on Fri Dec 15 18:30:05 GMT 2023 , Edited by admin on Fri Dec 15 18:30:05 GMT 2023
PRIMARY
CAS
6610-24-8
Created by admin on Fri Dec 15 18:30:05 GMT 2023 , Edited by admin on Fri Dec 15 18:30:05 GMT 2023
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PUBCHEM
23688479
Created by admin on Fri Dec 15 18:30:05 GMT 2023 , Edited by admin on Fri Dec 15 18:30:05 GMT 2023
PRIMARY
ECHA (EC/EINECS)
229-562-7
Created by admin on Fri Dec 15 18:30:05 GMT 2023 , Edited by admin on Fri Dec 15 18:30:05 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE