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

Details

Stereochemistry ACHIRAL
Molecular Formula C16H30O2
Molecular Weight 254.4088
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of PALMITOLEIC ACID

SMILES

CCCCCC/C(/[H])=C(/[H])\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 254.4088
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.

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 Sat Jun 26 03:33:37 UTC 2021
Edited
by admin
on Sat Jun 26 03:33:37 UTC 2021
Record UNII
209B6YPZ4I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PALMITOLEIC ACID
WHO-DD  
Systematic Name English
PALMITOLEIC ACID [WHO-DD]
Common Name English
CIS-PALMITOLEIC ACID
Systematic Name English
NSC-277452
Code English
PALMITOLEIC ACID (CONSTITUENT OF SPIRULINA) [DSC]
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 Sat Jun 26 03:33:37 UTC 2021 , Edited by admin on Sat Jun 26 03:33:37 UTC 2021
CFR 21 CFR 357.210
Created by admin on Sat Jun 26 03:33:37 UTC 2021 , Edited by admin on Sat Jun 26 03:33:37 UTC 2021
DSLD 2729 (Number of products:29)
Created by admin on Sat Jun 26 03:33:37 UTC 2021 , Edited by admin on Sat Jun 26 03:33:37 UTC 2021
Code System Code Type Description
DRUG BANK
DB04257
Created by admin on Sat Jun 26 03:33:37 UTC 2021 , Edited by admin on Sat Jun 26 03:33:37 UTC 2021
PRIMARY
ECHA (EC/EINECS)
206-765-9
Created by admin on Sat Jun 26 03:33:37 UTC 2021 , Edited by admin on Sat Jun 26 03:33:37 UTC 2021
PRIMARY
EPA CompTox
373-49-9
Created by admin on Sat Jun 26 03:33:37 UTC 2021 , Edited by admin on Sat Jun 26 03:33:37 UTC 2021
PRIMARY
MESH
C008757
Created by admin on Sat Jun 26 03:33:37 UTC 2021 , Edited by admin on Sat Jun 26 03:33:37 UTC 2021
PRIMARY
PUBCHEM
445638
Created by admin on Sat Jun 26 03:33:37 UTC 2021 , Edited by admin on Sat Jun 26 03:33:37 UTC 2021
PRIMARY
WIKIPEDIA
PALMITOLEIC ACID
Created by admin on Sat Jun 26 03:33:37 UTC 2021 , Edited by admin on Sat Jun 26 03:33:37 UTC 2021
PRIMARY
FDA UNII
209B6YPZ4I
Created by admin on Sat Jun 26 03:33:37 UTC 2021 , Edited by admin on Sat Jun 26 03:33:37 UTC 2021
PRIMARY
NCI_THESAURUS
C68408
Created by admin on Sat Jun 26 03:33:37 UTC 2021 , Edited by admin on Sat Jun 26 03:33:37 UTC 2021
PRIMARY
CAS
373-49-9
Created by admin on Sat Jun 26 03:33:37 UTC 2021 , Edited by admin on Sat Jun 26 03:33:37 UTC 2021
PRIMARY
Related Record Type Details
LIPID -> FATTY ACID
IOOC limits
LIPID -> FATTY ACID
MAY BE PRESENT
USP
LIPID -> FATTY ACID
Values given are in undefined precent. Average is typical for U.S. Sunflower oil.
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
LIPID -> FATTY ACID
VARIES ACCORDING TO METHOD OF EXTRACTION
LIPID -> FATTY ACID
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
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)
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)
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
Values are % of total.
PARENT -> CONSTITUENT ALWAYS PRESENT
USP