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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
Behavioral, metabolic, and molecular correlates of lower insulin sensitivity in Mexican-Americans.
2002 Oct
Beneficial effect of oleoylated lipids on paraoxonase 1: protection against oxidative inactivation and stabilization.
2003 Oct 15
Preferential inhibition of paraoxonase activity of human paraoxonase 1 by negatively charged lipids.
2004 Dec
Unsaturated fatty acids phosphorylate and destabilize ABCA1 through a phospholipase D2 pathway.
2005 Oct 28
Methotrexate-induced alterations in beta-oxidation correlate with cognitive abilities in children with acute lymphoblastic leukemia.
2008 Apr
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 Thu Jul 06 01:43:01 UTC 2023
Edited
by admin
on Thu Jul 06 01:43:01 UTC 2023
Record UNII
9KXN90LI9Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SODIUM PALMITOLEATE
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID901016441
Created by admin on Thu Jul 06 01:43:01 UTC 2023 , Edited by admin on Thu Jul 06 01:43:01 UTC 2023
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FDA UNII
9KXN90LI9Y
Created by admin on Thu Jul 06 01:43:01 UTC 2023 , Edited by admin on Thu Jul 06 01:43:01 UTC 2023
PRIMARY
CAS
6610-24-8
Created by admin on Thu Jul 06 01:43:01 UTC 2023 , Edited by admin on Thu Jul 06 01:43:01 UTC 2023
PRIMARY
PUBCHEM
23688479
Created by admin on Thu Jul 06 01:43:01 UTC 2023 , Edited by admin on Thu Jul 06 01:43:01 UTC 2023
PRIMARY
ECHA (EC/EINECS)
229-562-7
Created by admin on Thu Jul 06 01:43:01 UTC 2023 , Edited by admin on Thu Jul 06 01:43:01 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE