petroselinic acid
6-octadecenoic acid
Identification
| Name | petroselinic acid |
| IUPAC | octadec-6-enoic acid |
| CAS Number | 593-40-8 |
| FDA UNII | Search |
| Molecular Formula | C18 H34 O2 |
| Molecular Weight | 282.46738000 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 399.00 to 400.00 °C. @ 760.00 mm Hg (est) |
| Flash Point | 564.00 °F. TCC ( 295.80 °C. ) (est) |
| logP (o/w) | 7.481 (est) |
| Soluble in | alcohol |
| Insoluble in | water |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for petroselinic acid usage levels up to | not for fragrance use. |
| Recommendation for petroselinic acid flavor usage levels up to | not for flavor use. |
No supplier data available
Potential Uses
Natural Occurrence
Synonyms
octadec-6-enoic acid
6-
octadecenoic acid
PubMed:
Evaluation of coriander spice as a functional food by using in vitro bioassays.
PubMed:
Fatty Acid Composition and Volatile Constituents of Protaetia brevitarsis Larvae.
PubMed:
Effects of dietary supplementation of coriander oil, in canola oil diets, on the metabolism of [1-(14)C] 18:3n-3 and [1-(14)C] 18:2n-6 in rainbow trout hepatocytes.
PubMed:
Evaluation of the impact of dietary petroselinic acid on the growth performance, fatty acid composition, and efficacy of long chain-polyunsaturated fatty acid biosynthesis of farmed Nile tilapia.
PubMed:
Gas chromatography-mass spectrometry analysis on compounds in volatile oils extracted from yuan zhi (radix polygalae) and shi chang pu (acorus tatarinowii) by supercritical CO2.
PubMed:
Coriander (Coriandrum sativum L.): a potential source of high-value components for functional foods and nutraceuticals--a review.
PubMed:
Identification of Î6-monounsaturated fatty acids in human hair and nail samples by gas-chromatography-mass-spectrometry using ionic-liquid coated capillary column.
PubMed:
Essential oils and fatty acids composition of Tunisian and Indian cumin (Cuminum cyminum L.) seeds: a comparative study.
PubMed:
Specific unsaturated fatty acids enforce the transdifferentiation of human cancer cells toward adipocyte-like cells.
PubMed:
Resolution and quantification of isomeric fatty acids by silver ion HPLC: fatty acid composition of aniseed oil (Pimpinella anisum, Apiaceae).
PubMed:
Sulfonic-hydroxyl-type heterogemini surfactants synthesized from unsaturated fatty acids.
PubMed:
Fatty acid and essential oil composition of three Tunisian caraway (Carum carvi L.) seed ecotypes.
PubMed:
Using a novel petroselinic Acid embedded cellulose acetate membrane to mimic plant partitioning and in vivo uptake of polycyclic aromatic hydrocarbons.
PubMed:
Substrate selectivity of 5-hydroxyeicosanoid dehydrogenase and its inhibition by 5-hydroxy-Delta6-long-chain fatty acids.
PubMed:
Infrared spectroscopy and differential scanning calorimetry studies of binary combinations of cis-6-octadecenoic acid and octadecanoic acid.
PubMed:
Lipids as renewable resources: current state of chemical and biotechnological conversion and diversification.
PubMed:
Genomic structures and characterization of the 5'-flanking regions of acyl carrier protein and Delta4-palmitoyl-ACP desaturase genes from Coriandrum sativum.
PubMed:
A multifunctional acyl-acyl carrier protein desaturase from Hedera helix L. (English ivy) can synthesize 16- and 18-carbon monoene and diene products.
PubMed:
Geranium sanguineum (Geraniaceae) seed oil: a new source of petroselinic and vernolic acid.
PubMed:
[2,4-Dienoyl-CoA reductases: from discovery toward pathophysiological significance].
PubMed:
Quantitative 2H NMR analysis of deuterium distribution in petroselinic acid isolated from parsley seed.
PubMed:
What limits production of unusual monoenoic fatty acids in transgenic plants?
PubMed:
Base-catalyzed derivatization methodology for FA analysis. application to milk fat and celery seed lipid TAG.
PubMed:
Novel methoxylated FA from the Caribbean sponge Spheciospongia cuspidifera.
PubMed:
Dibutyrate derivatization of monoacylglycerols for the resolution of regioisomers of oleic, petroselinic, and cis-vaccenic acids.
PubMed:
An unusual seed-specific 3-ketoacyl-ACP synthase associated with the biosynthesis of petroselinic acid in coriander.
PubMed:
The genus Thapsia as a source of petroselinic acid.
PubMed:
Inhibition of topoisomerases by fatty acids.
PubMed:
Function of human mitochondrial 2,4-dienoyl-CoA reductase and rat monofunctional Delta3-Delta2-enoyl-CoA isomerase in beta-oxidation of unsaturated fatty acids.
PubMed:
Adipose tissue triacylglycerols of rats are modulated differently by dietary isomeric octadecenoic acids from coriander oil and high oleic sunflower oil.
PubMed:
Alternatives to the isomerase-dependent pathway for the beta-oxidation of oleic acid are dispensable in Saccharomyces cerevisiae. Identification of YOR180c/DCI1 encoding peroxisomal delta(3,5)-delta(2,4)-dienoyl-CoA isomerase.
PubMed:
Sources of NADPH and expression of mammalian NADP+-specific isocitrate dehydrogenases in Saccharomyces cerevisiae.
PubMed:
Skin penetration enhancing action of cis-unsaturated fatty acids with omega-9, and omega-12-chain lengths.
PubMed:
Peroxisomal beta-oxidation of polyunsaturated fatty acids in Saccharomyces cerevisiae: isocitrate dehydrogenase provides NADPH for reduction of double bonds at even positions.
PubMed:
Identification of the novel 7-methyl-6-octadecenoic acid in Holothuria mexicana.
PubMed:
Fat infiltration in liver of rats induced by different dietary plant oils: high oleic-, medium oleic- and high petroselinic acid-oils.
PubMed:
Isolation and characterization of a delta-9 fatty acid desaturase gene from the oleaginous yeast Cryptococcus curvatus CBS 570.
PubMed:
Petroselinic acid from dietary triacylglycerols reduces the concentration of arachidonic acid in tissue lipids of rats.
PubMed:
Transactivation by PPAR/RXR heterodimers in yeast is potentiated by exogenous fatty acid via a pathway requiring intact peroxisomes.
PubMed:
Apparent Role of Phosphatidylcholine in the Metabolism of Petroselinic Acid in Developing Umbelliferae Endosperm.
PubMed:
Specificities of the Acyl-Acyl Carrier Protein (ACP) Thioesterase and Glycerol-3-Phosphate Acyltransferase for Octadecenoyl-ACP Isomers (Identification of a Petroselinoyl-ACP Thioesterase in Umbelliferae).
PubMed:
Metabolic Evidence for the Involvement of a [delta]4-Palmitoyl-Acyl Carrier Protein Desaturase in Petroselinic Acid Synthesis in Coriander Endosperm and Transgenic Tobacco Cells.
PubMed:
Petroselinic acid biosynthesis and production in transgenic plants.
PubMed:
Heteronuclear NMR analysis of unsaturated fatty acids in poly(3-hydroxyalkanoates). Study of beta-oxidation in Pseudomonas putida.
PubMed:
Expression of a coriander desaturase results in petroselinic acid production in transgenic tobacco.
PubMed:
[Chemical and biological properties of coriander fatty oil].
PubMed:
Lipase from Brassica napus L. discriminates against cis-4 and cis-6 unsaturated fatty acids and secondary and tertiary alcohols.
PubMed:
Evidence for the essential function of 2,4-dienoyl-coenzyme A reductase in the beta-oxidation of unsaturated fatty acids in vivo. Isolation and characterization of an Escherichia coli mutant with a defective 2,4-dienoyl-coenzyme A reductase.
PubMed:
Isolation and characterization of a novel four-chain ether lipid from Clostridium butyricum: the phosphatidylglycerol acetal of plasmenylethanolamine.
PubMed:
Lipid shape as a determinant of lipid composition in Clostridium butyricum. The effects of incorporation of various fatty acids on the ratios of the major ether lipids.
PubMed:
Incorporation of cis-octadecenoic acids into the rat liver mitochondrial membrane phospholipids and adipose tissue triglycerides.
PubMed:
Unusual fatty acids in the lipids from organs and cell cultures ofPetroselinum crispum.
PubMed:
Effect of fatty acids on growth of Japanese encephalitis virus cultivated in BHK-21 cells and phospholipid metabolism of the infected cells.
PubMed:
Temperature-dependent changes in activation energies of the transport systems for nucleosides, choline and deoxyglucose of cultured Novikoff rat hepatoma cells and effects of cytochalasin B and lipid solvents.
PubMed:
Studies on the specificity of a lipase system fromGeotrichum candidum.
PubMed:
Determination of petroselinic acid by microreactor chromatography.