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
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-;
| 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
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: map04540 |
|||
Target ID: CHEMBL5346 |
|||
Target ID: CHEMBL1075142 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Preventing | Palmitoleic Acid Approved UseA purified form of omega-7 to help combat type II diabetes, atherosclerosis and metabolic syndrome. |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
|
| 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 induce calcium influx into keratinocytes and cause abnormal differentiation of epidermis. | 2005 May |
|
| 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
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
| Substance Class |
Chemical
Created
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admin
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| Record UNII |
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| Record Status |
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PARENT -> SALT/SOLVATE |
