U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

Description

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

Hofstädter, P.G.
3
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

2014
494
Targets

Targets

Primary TargetPharmacologyConditionPotency
Modulator
828
Inhibitor
8297
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase I
428
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Preventing
Approved
8429
Palmitoleic Acid

Approved Use

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

PubMed

TitleDatePubMed
Clinical pharmacology of antibiotics and other drugs in cystic fibrosis.
1988 May
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
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
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
A pilot study of GC/MS-based serum metabolic profiling of acute rejection in renal transplantation.
2008 Apr
Antimicrobial activity of n-6, n-7 and n-9 fatty acids and their esters for oral microorganisms.
2010 Aug
Patents

Patents

JP2000136132A
3
JP2001172176A
5
JP2001200289A
3
JP2001245687A
5
JP2001504461A
3
JP2002501019A
7
JP2002514229A
11
JP2002536075A
14
JP2002537070A
15
JP2003104830A
3
JP2004231537A
3
JP2005500988A
8
JP2005509588A
19
JP2006232860A
8
JP2006311924A
4
JP2006509069A
11
JP2007070486A
3
JP2009149599A
9
JP2009504194A
3
JP2009522777A
14
JP2010275201A
3
JP2011527716A
10
JP2011529503A
6
JP2012500645A
3
JP2012500647A
3
JP2513877B2
11
JP2557674B2
3
JP3621425B2
10
JP4111349B2
9
JP4504197B2
3
JP4690404B2
11
JP4690405B2
9
JP4806519B2
14
JP4838936B2
15
JP5346290B2
3
JPH00622772A
3
JPH01108991A
3
JPH01146818A
3
JPH01163176A
3
JPH01187089A
3
JPH01238511A
3
JPH02108613A
3
JPH02178338A
7
JPH02188574A
7
JPH02247111A
3
JPH0232199A
3
JPH0241169A
3
JPH026404A
4
JPH0381286A
12
JPH04108394A
3
JPH04135453A
3
JPH0633087A
3
JPS63145210A
3

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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:56:34 GMT 2023
Edited
by admin
on Fri Dec 15 15:56:34 GMT 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 GMT 2023 , Edited by admin on Fri Dec 15 15:56:34 GMT 2023
CFR 21 CFR 357.210
Created by admin on Fri Dec 15 15:56:34 GMT 2023 , Edited by admin on Fri Dec 15 15:56:34 GMT 2023
DSLD 2729 (Number of products:29)
Created by admin on Fri Dec 15 15:56:34 GMT 2023 , Edited by admin on Fri Dec 15 15:56:34 GMT 2023
Code System Code Type Description
DAILYMED
209B6YPZ4I
Created by admin on Fri Dec 15 15:56:34 GMT 2023 , Edited by admin on Fri Dec 15 15:56:34 GMT 2023
PRIMARY
CHEBI
28716
Created by admin on Fri Dec 15 15:56:34 GMT 2023 , Edited by admin on Fri Dec 15 15:56:34 GMT 2023
PRIMARY
DRUG BANK
DB04257
Created by admin on Fri Dec 15 15:56:34 GMT 2023 , Edited by admin on Fri Dec 15 15:56:34 GMT 2023
PRIMARY
RXCUI
2475955
Created by admin on Fri Dec 15 15:56:34 GMT 2023 , Edited by admin on Fri Dec 15 15:56:34 GMT 2023
PRIMARY
ECHA (EC/EINECS)
206-765-9
Created by admin on Fri Dec 15 15:56:34 GMT 2023 , Edited by admin on Fri Dec 15 15:56:34 GMT 2023
PRIMARY
EPA CompTox
DTXSID0041197
Created by admin on Fri Dec 15 15:56:34 GMT 2023 , Edited by admin on Fri Dec 15 15:56:34 GMT 2023
PRIMARY
MESH
C008757
Created by admin on Fri Dec 15 15:56:34 GMT 2023 , Edited by admin on Fri Dec 15 15:56:34 GMT 2023
PRIMARY
NSC
277452
Created by admin on Fri Dec 15 15:56:34 GMT 2023 , Edited by admin on Fri Dec 15 15:56:34 GMT 2023
PRIMARY
PUBCHEM
445638
Created by admin on Fri Dec 15 15:56:34 GMT 2023 , Edited by admin on Fri Dec 15 15:56:34 GMT 2023
PRIMARY
WIKIPEDIA
PALMITOLEIC ACID
Created by admin on Fri Dec 15 15:56:34 GMT 2023 , Edited by admin on Fri Dec 15 15:56:34 GMT 2023
PRIMARY
FDA UNII
209B6YPZ4I
Created by admin on Fri Dec 15 15:56:34 GMT 2023 , Edited by admin on Fri Dec 15 15:56:34 GMT 2023
PRIMARY
NCI_THESAURUS
C68408
Created by admin on Fri Dec 15 15:56:34 GMT 2023 , Edited by admin on Fri Dec 15 15:56:34 GMT 2023
PRIMARY
CAS
373-49-9
Created by admin on Fri Dec 15 15:56:34 GMT 2023 , Edited by admin on Fri Dec 15 15:56:34 GMT 2023
PRIMARY
Related Record Type Details
AVOCADO OIL
LIPID -> FATTY ACID
VARIES ACCORDING TO METHOD OF EXTRACTION
FISH OIL
LIPID -> FATTY ACID
MAY BE PRESENT
USP
SUNFLOWER OIL
LIPID -> FATTY ACID
Values given are in undefined precent. Average is typical for U.S. Sunflower oil.
CANOLA OIL
LIPID -> FATTY ACID
PALM OIL
LIPID -> FATTY ACID
Values are % of total.
OLIVE OIL
LIPID -> FATTY ACID
EUROPEAN SOURCE
SAW PALMETTO
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
COTTONSEED OIL
LIPID -> FATTY ACID
G Jurriens and ACJ Kroesen, J Am Oil Chem Soc, 42(9)(1965)(average value). Range values as of FAO/WHO Codex Alimentarius Committee on commercial fats and oils.(unspecified percent)
COD LIVER OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
SOYBEAN OIL
LIPID -> FATTY ACID
Values are % of weight of fatty acid composition. O?Connor, RT, Herb, SF; J Am Oil Chem Soc 47, 186A, 195A, 197A(1970)(range) Brignoli, CA et al: J Am Diet Assoc 68, 224(1976)(average)
Structure of SODIUM PALMITOLEATE
SALT/SOLVATE -> PARENT
Structure of POTASSIUM PALMITOLEATE
SALT/SOLVATE -> PARENT
KRILL OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
SPIRULINA
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966