Np mrd loader

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.
Record Information
Version1.0
Created at2006-05-22 14:17:35 UTC
Updated at2024-05-05 00:32:37 UTC
NP-MRD IDNP0000010
Secondary Accession NumbersNone
Natural Product Identification
Common NamePetroselinic acid
DescriptionPetroselinic acid, also known as (6Z)-Octadecenoic acid, is an 18-carbon unsaturated fatty acid that occurs naturally in several animal and vegetable fats and oils. It is a white powder and is commercially available. In chemical terms, petroselinic acid is classified as a monounsaturated omega-12 fatty acid, abbreviated as 18:1 Cis-6. Petroselinic acid is a positional isomer of oleic acid. The term "petroselinic" means related to, or derived from, oil of Petroselinum, or oil of parsley. Petroselinic acid was first isolated from parsley seed oil in 1909. Petroselinic acid occurs in high amounts in plants in the Apiaceae family (a family of mostly aromatic flowering plants named after the genus Apium and commonly known as the celery, carrot or parsley family), Araliaceae (a family of flowering plants composed of about 43 genera and around 1500 species consisting of primarily woody plants and some herbaceous plants), Griselinia (Griseliniaceae) and in Garryaceae. The occurrence of petroselinic acid as the major fatty acid is used in chemosystematics as a proof of a close relationship of several families within the Apiales as well as within the Garryales. Petroselonic acid has been found in coriander (Coriandrum sativum) and cumin (Cuminum cyminum) and caraway seeds. In addition, petroselinic acid has been found in minor amounts in several fats of plant and animal origin, including in human sources. Petroselinic acid is an important oleochemical material for the food, cosmetics, chemistry and pharmaceutical industry (PMID: 16604360 ) As it can be easily processed into lauric and adipinic acid.
Structure
Thumb
Synonyms
ValueSource
18:1N-6ChEBI
6-OctadecensaeureChEBI
C18:1N-6ChEBI
Octadec-6-ensaeureChEBI
PetroselinateGenerator
Octadec-6-enoateHMDB
Petroselinic acid, (e)-isomerHMDB
Petroselinic acid, sodium salt, (Z)-isomerHMDB
Petroselenic acidHMDB
Petroselinic acid, (Z)-isomerHMDB
Petroselinic acidMeSH
Chemical FormulaC18H34O2
Average Mass282.4680 Da
Monoisotopic Mass282.25588 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number593-39-5
SMILESNot Available
InChI Identifier
InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h12-13H,2-11,14-17H2,1H3,(H,19,20)
InChI KeyCNVZJPUDSLNTQU-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
Species
Species of Origin
Species NameSourceReference
Agaricus blazei
Anas platyrhynchos
Anatidae
Anethum graveolensFooDB
Anser anser
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Aralia spinosaKNApSAcK Database
Bison bison
Bos taurus
Bos taurus X Bison bison
Bubalus bubalis
Bupleurum chinenseKNApSAcK Database
Capra aegagrus hircus
Carum carviFooDB
Cervidae
Cervus canadensis
Chlamydomonas reinhardtii
Columba
Columbidae
Coriandrum sativum
Coriandrum sativum L.FooDB
Cuminum cyminumFooDB
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dromaius novaehollandiae
Eleutherococcus sessiliflorus
Equus caballus
Foeniculum vulgareFooDB
Gallus gallus
Heracleum sphondylium
Hibiscus syriacus
Lagopus muta
Leporidae
Lepus timidus
Macrococculus pomiferus
Melanitta fusca
Meleagris gallopavo
Momordica charantiaFooDB
Myristica fragrans
Myrrhis odorata
Nepeta cataria
Numida meleagris
Odocoileus
Oryctolagus
Ovis aries
Pastinaca sativaFooDB
Petroselinum crispumKNApSAcK Database
Phasianidae
Phasianus colchicus
Pimpinella anisumFooDB
Struthio camelus
Sus scrofa
Sus scrofa domestica
Teucrium royleanum
Thapsia villosa
Tritrichomonas foetus
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point29.8 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
HMDB IDHMDB0002080
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012765
KNApSAcK IDC00001235
Chemspider ID11144
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPetroselinic acid
METLIN IDNot Available
PubChem Compound11634
PDB IDNot Available
ChEBI ID36022
Good Scents IDNot Available
References
General References
  1. Metzger JO, Bornscheuer U: Lipids as renewable resources: current state of chemical and biotechnological conversion and diversification. Appl Microbiol Biotechnol. 2006 Jun;71(1):13-22. Epub 2006 Apr 8. [PubMed:16604360 ]
  2. Ping F, Li Y, Cao Y, Shang J, Zhang Z, Yuan Z, Wang W, Guo Y: Metabolomics Analysis of the Development of Sepsis and Potential Biomarkers of Sepsis-Induced Acute Kidney Injury. Oxid Med Cell Longev. 2021 Apr 23;2021:6628847. doi: 10.1155/2021/6628847. eCollection 2021. [PubMed:33981387 ]
  3. Saini RK, Assefa AD, Keum YS: Spices in the Apiaceae Family Represent the Healthiest Fatty Acid Profile: A Systematic Comparison of 34 Widely Used Spices and Herbs. Foods. 2021 Apr 14;10(4). pii: foods10040854. doi: 10.3390/foods10040854. [PubMed:33920058 ]
  4. Erbiai EH, da Silva LP, Saidi R, Lamrani Z, Esteves da Silva JCG, Maouni A: Chemical Composition, Bioactive Compounds, and Antioxidant Activity of Two Wild Edible Mushrooms Armillaria mellea and Macrolepiota procera from Two Countries (Morocco and Portugal). Biomolecules. 2021 Apr 14;11(4). pii: biom11040575. doi: 10.3390/biom11040575. [PubMed:33920034 ]
  5. Berriozabalgoitia A, Gordoa JCR, Renobales M, Amores G, Barron LJR, Amiano P, Dorronsoro M, Perea Z, Virto M: The Sum of Plasma Fatty Acids iso16:0, iso17:0, trans11-18:1, cis9, trans11-CLA, and cis6-18:1 as Biomarker of Dairy Intake Established in an Intervention Study and Validated in the EPIC Cohort of Gipuzkoa. Nutrients. 2021 Feb 22;13(2). pii: nu13020702. doi: 10.3390/nu13020702. [PubMed:33671693 ]