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
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-
| 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
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: map04540 |
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Target ID: CHEMBL5346 |
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Target ID: CHEMBL1075142 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Preventing | Palmitoleic Acid Approved UseA purified form of omega-7 to help combat type II diabetes, atherosclerosis and metabolic syndrome. |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Antimicrobial activity of n-6, n-7 and n-9 fatty acids and their esters for oral microorganisms. | 2010-08 |
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| Methotrexate-induced alterations in beta-oxidation correlate with cognitive abilities in children with acute lymphoblastic leukemia. | 2008-04 |
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| A pilot study of GC/MS-based serum metabolic profiling of acute rejection in renal transplantation. | 2008-04 |
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| Unsaturated fatty acids phosphorylate and destabilize ABCA1 through a phospholipase D2 pathway. | 2005-10-28 |
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| Unsaturated fatty acids induce calcium influx into keratinocytes and cause abnormal differentiation of epidermis. | 2005-05 |
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| Preferential inhibition of paraoxonase activity of human paraoxonase 1 by negatively charged lipids. | 2004-12 |
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| Beneficial effect of oleoylated lipids on paraoxonase 1: protection against oxidative inactivation and stabilization. | 2003-10-15 |
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| Behavioral, metabolic, and molecular correlates of lower insulin sensitivity in Mexican-Americans. | 2002-10 |
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| Selective mobilisation of fatty acids from human adipose tissue. | 2001-04 |
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| 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. | 2000-09 |
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| 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. | 1998-09 |
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| Determination of free fatty acids in human bile by high-performance liquid chromatography. | 1998-03 |
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| Platelet trans fatty acids in relation to angiographically assessed coronary artery disease. | 1996-02 |
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| Fatty acids and fibrates are potent inducers of transcription of the phosphenolpyruvate carboxykinase gene in adipocytes. | 1995-12-01 |
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| Fatty acid composition in serum lipids and adipose tissue in severe obesity before and after six weeks of weight loss. | 1989 |
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| Clinical pharmacology of antibiotics and other drugs in cystic fibrosis. | 1988-05 |
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
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| Record UNII |
209B6YPZ4I
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| Record Status |
Validated (UNII)
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NCI_THESAURUS |
C68382
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CFR |
21 CFR 357.210
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DSLD |
2729 (Number of products:29)
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209B6YPZ4I
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28716
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DB04257
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2475955
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206-765-9
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DTXSID0041197
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C008757
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277452
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445638
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PALMITOLEIC ACID
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209B6YPZ4I
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C68408
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373-49-9
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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LIPID -> FATTY ACID |
MAY BE PRESENT
USP
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LIPID -> FATTY ACID | |||
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LIPID -> FATTY ACID |
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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LIPID -> FATTY ACID | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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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)
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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)
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID |
