Myristoleic acid

MUFA14:1Ω-5

  Overview

Stats

MUFA
Type
14
Carbons
1
Double bonds
0
Bis-allylic sites
226.35
Weight · g/mol
—
Melting point
C14H26O2
Formula

Also known as

IUPAC (Z)-tetradec-9-enoic acid
Synonyms

  At a Glance

Key Points

An uncommon omega-5 fatty acid; a major component of saw palmetto and some Myristicaceae seed oils.

Source

Found in fish & seafood.

Type

Long-chain monounsaturated fatty acid with 14 carbons and one cis double bond, an omega-5 fatty acid.

Identification

  Synonyms

Common Name Myristoleic acid
IUPAC Name (Z)-tetradec-9-enoic acid
Traditional Name —
Other Synonyms
  • cis-9-tetradecenoic acid

  External IDs

General References
Lipids
Lipid Maps LMFA01030051
Lipid Bank DFA0073
Swiss Lipids 000000856
PlantFA ID —
Food & Nutrition
FooDB FDB012633
INFOODS —
Chemistry / Compounds
PubChem CID 5281119
CAS 544-64-9
ChEBI 27781
ChEMBL CHEMBL456732
ChemSpider 4444564
InChIKey —
ZINC ID ZINC000004529321
NIKKAJI ID J11.362J
PDBe MYZ
UCI (UniChem) 195000
SureChEMBL 109270
CCDC —
NMRShiftDB 60018543
Metabolites & Pathways
HMDB HMDB0002000
METLIN 6424
RefMet ID —
RefMet Name —
MetaboLights ID MTBLC27781
BioCyc/MetaCyc —
MetaNetX ID MNXM62836
BiGG ID —
KEGG C08322
KNApSAcK C00001229
Reactome ID —
Drugs & Pharmacology
DrugBank —
DrugCentral —
BindingDB 50269530
Guide to Pharm —
Probes & Drugs PD061154
Clinical & Medical
SNOMED-CT —
MeSH —
NCIt Code C68394
Regulatory
NIH UNII (USA) RF23WGD123
FDA SRS (USA) RF23WGD123
NHPID (Canada) —
DTXSID (USA) DTXSID5041568
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort Molport-003-958-711
eMolecules 591845
Mcule —
ChemicalBook CB2447081
MedChemExpress HY-113332

Isomers of 14:1 (2)

Other fatty acids sharing the 14:1 notation — differing by double-bond position, geometry (cis/trans), or conjugation.

Name Geometry Trans Structure PubChem
Current Fatty Acid
Myristoleic acid
(Z)-tetradec-9-enoic acid
 9Z —
5281119
Category —
Conjugation Type —
SMILES CCCC\C=C/CCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Geometric (1)
Myristelaidic acid
(E)-tetradec-9-enoic acid
 9E Trans
5312402
Category —
Conjugation Type —
SMILES CCCC/C=C/CCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.

Chemical Properties

Name(s):
Common Name Myristoleic acid
Simple Notation 14:1
Notation 14:1(n-5)
IUPAC Name (Z)-tetradec-9-enoic acid
Structure:
Molecular C14H26O2
Structure CH3(CH2)3CH=CH(CH2)7COOH
SMILES CCCC\C=C/CCCCCCCC(=O)O
Cis / Trans cis
E-Z 9Z
Physical:
Weight 226.35 g/mol
Reactivity
Double Bonds 1
Bis-Allylic Carbons 0
Beta-Oxidation
Beta Oxidation Cycles 6
ATP Yield (Net) 90.5 ATP