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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 of PALMITOLEIC ACID

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

Molecular Formula C16H30O2
Molecular Weight 254.4082
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
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
Fatty acid composition in serum lipids and adipose tissue in severe obesity before and after six weeks of weight loss.
1989
Fatty acids and fibrates are potent inducers of transcription of the phosphenolpyruvate carboxykinase gene in adipocytes.
1995 Dec 1
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
Selective mobilisation of fatty acids from human adipose tissue.
2001 Apr
Behavioral, metabolic, and molecular correlates of lower insulin sensitivity in Mexican-Americans.
2002 Oct
Preferential inhibition of paraoxonase activity of human paraoxonase 1 by negatively charged lipids.
2004 Dec
Unsaturated fatty acids induce calcium influx into keratinocytes and cause abnormal differentiation of epidermis.
2005 May
Methotrexate-induced alterations in beta-oxidation correlate with cognitive abilities in children with acute lymphoblastic leukemia.
2008 Apr
A pilot study of GC/MS-based serum metabolic profiling of acute rejection in renal transplantation.
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 Fri Dec 15 15:56:34 UTC 2023
Edited
by admin
on Fri Dec 15 15:56:34 UTC 2023
Record UNII
209B6YPZ4I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PALMITOLEIC ACID
WHO-DD  
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
Created by admin on Fri Dec 15 15:56:34 UTC 2023 , Edited by admin on Fri Dec 15 15:56:34 UTC 2023
CFR 21 CFR 357.210
Created by admin on Fri Dec 15 15:56:34 UTC 2023 , Edited by admin on Fri Dec 15 15:56:34 UTC 2023
DSLD 2729 (Number of products:29)
Created by admin on Fri Dec 15 15:56:34 UTC 2023 , Edited by admin on Fri Dec 15 15:56:34 UTC 2023
Code System Code Type Description
DAILYMED
209B6YPZ4I
Created by admin on Fri Dec 15 15:56:34 UTC 2023 , Edited by admin on Fri Dec 15 15:56:34 UTC 2023
PRIMARY
CHEBI
28716
Created by admin on Fri Dec 15 15:56:34 UTC 2023 , Edited by admin on Fri Dec 15 15:56:34 UTC 2023
PRIMARY
DRUG BANK
DB04257
Created by admin on Fri Dec 15 15:56:34 UTC 2023 , Edited by admin on Fri Dec 15 15:56:34 UTC 2023
PRIMARY
RXCUI
2475955
Created by admin on Fri Dec 15 15:56:34 UTC 2023 , Edited by admin on Fri Dec 15 15:56:34 UTC 2023
PRIMARY
ECHA (EC/EINECS)
206-765-9
Created by admin on Fri Dec 15 15:56:34 UTC 2023 , Edited by admin on Fri Dec 15 15:56:34 UTC 2023
PRIMARY
EPA CompTox
DTXSID0041197
Created by admin on Fri Dec 15 15:56:34 UTC 2023 , Edited by admin on Fri Dec 15 15:56:34 UTC 2023
PRIMARY
MESH
C008757
Created by admin on Fri Dec 15 15:56:34 UTC 2023 , Edited by admin on Fri Dec 15 15:56:34 UTC 2023
PRIMARY
NSC
277452
Created by admin on Fri Dec 15 15:56:34 UTC 2023 , Edited by admin on Fri Dec 15 15:56:34 UTC 2023
PRIMARY
PUBCHEM
445638
Created by admin on Fri Dec 15 15:56:34 UTC 2023 , Edited by admin on Fri Dec 15 15:56:34 UTC 2023
PRIMARY
WIKIPEDIA
PALMITOLEIC ACID
Created by admin on Fri Dec 15 15:56:34 UTC 2023 , Edited by admin on Fri Dec 15 15:56:34 UTC 2023
PRIMARY
FDA UNII
209B6YPZ4I
Created by admin on Fri Dec 15 15:56:34 UTC 2023 , Edited by admin on Fri Dec 15 15:56:34 UTC 2023
PRIMARY
NCI_THESAURUS
C68408
Created by admin on Fri Dec 15 15:56:34 UTC 2023 , Edited by admin on Fri Dec 15 15:56:34 UTC 2023
PRIMARY
CAS
373-49-9
Created by admin on Fri Dec 15 15:56:34 UTC 2023 , Edited by admin on Fri Dec 15 15:56:34 UTC 2023
PRIMARY
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