Stearidonic Acid (HCID 5312508)

Overview

All-cis-octadeca-6,9,12,15-tetraenoic acid is an octadecatetraenoic acid having four double bonds located at positions 6, 9, 12 and 15 (the all-cis-isomer). It has been isolated from Lithospermum officinale and fish oils. It has a role as a mouse metabolite, a plant metabolite and a Daphnia galeata metabolite. It is a long-chain fatty acid, an omega-3 fatty acid and an octadecatetraenoic acid. It is a conjugate acid of a (6Z,9Z,12Z,15Z)-octadecatetraenoate.

Names & identifiers

Preferred name: Stearidonic Acid
IUPAC: (6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoic acid
English name: STEARIDONIC ACID
Molecular formula: C18H28O2
Molecular weight: 276.41

Names & synonyms

Stearidonic acid20290-75-96Z,9Z,12Z,15Z-octadecatetraenoic acidP4CEK3495ORefChem:185402Moroctic acid(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoic acid6,9,12,15-Octadecatetraenoic acid, (6Z,9Z,12Z,15Z)-(6Z,9Z,12Z,15Z)-Octadecatetraenoic acidFA 18:4all-cis-6,9,12,15-Octadecatetraenoic acid111174-40-4

Show more names

18:4ω318:4(n-3)Chebi:32389Stearidonic Acid (Moroctic Acid)6C,9C,12C,15C-OCTADECATETRAENOIC ACID

all-cis-octadeca-6,9,12,15-tetraenoic acidUNII-P4CEK3495O6cis Stearidonic acidstearidonic acid C18:4Stearidonic acid, >=99%SCHEMBL29226STEARIDONIC ACID [MI]CHEMBL484430

Database identifiers

CAS: 20290-75-9
PubChem CID: 5312508
DTXSID: DTXSID20920493
ChEMBL: CHEMBL484430
ChEBI: CHEBI:32389
UNII: P4CEK3495O
EC Number: 606-502-1
Nikkaji: J381.480G

Properties

Computed structural properties

XLogP: 5.2
Topological polar surface area: 37.3 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 2
Rotatable bonds: 12
Heavy atoms: 20
Formal charge: 0
Complexity: 335

Experimental & physicochemical properties

Lipids · 2 items

Lipids -> Unambiguous Lipids

Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Unsaturated fatty acids [FA0103]

Endocrine DisruptorsPotential endocrine disrupting compound

Physical DescriptionLiquid

Collision Cross Section174.8 Å² [M-H]- [CCS Type: DT; Buffer gas: N2; Sample Type: Human plasma; Dataset: Unambiguous Lipids]

Physicochemical properties

Melting point: 200 ℃ · 200℃ (decomposition)
Boiling point: 382.5 · 382.5±11.0 °C(Predicted)
Density: 0.9334 g/cm3 · 0.9334 g/cm3 (15 ºC)
refractive index: 1.493 · 1.4930 (589.3 nm 15℃)
Flash point: 17 °C · 17 °C
storage temp.: -20 °C · -20°C
solubility: Chloroform (Slightly)
form: liquid
pka: 4.74 · 4.74±0.10(Predicted)
color: Clear Colorless to Light Yellow
Stability: Light Sensitive
InChI: 1S/C18H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10,12-13H,2,5,8,11,14-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-,13-12-
InChIKey: JIWBIWFOSCKQMA-LTKCOYKYSA-N
SMILES: CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O
LogP: 5.89 · 5.890 (est)
FDA UNII: 4 CEK3495O · P4CEK3495O
UNSPSC Code: 12352211 · 12352211
NACRES: 25 · NA.25
Symbol(GHS): 2 · GHS02
Signal word: Danger
Hazard statements: 225 · H225
Precautionary statements: 210 · P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P370+P378-P403+P235-P501
Hazard Codes: F
Risk Statements: 11 · 11
Safety Statements: 7 · 7-16
RIDADR: 1170 · UN 1170 3/PG 2
WGK Germany: 3 · 3
Storage Class: 10 · 10 - Combustible liquids

Safety & regulation

Safety data

wgk: 3
ridadr: UN 1170 3/PG 2
risk_code: 11
Signal word: Danger
Symbol(GHS): GHS02
hazard_code: F
safety_code: 7-16
Storage Class: 10 - Combustible liquids
Hazard statements: H225
Precautionary statements: P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P370+P378-P403+P235-P501

Chemistry & industry

Pharmacology

Tissue LocationsPlacenta

Cellular LocationsExtracellular

Metabolite Pathwaysalpha-Linolenic acid metabolism

Applications · 3 items

DescriptionStearidonic acid (SDA) is an ω-3 fatty acid, sometimes called moroctic acid. It is biosynthesized from alpha-linolenic acid by the enzyme delta-6-desaturase. Natural sources of this fatty acid are the seed oils of hemp, blackcurrant, corn gromwell and echium, and the cyanobacterium Spirulina.

UsesStearidonic Acid onic acid is present in small amounts in seed oils.

UsesA 18-carbon, ω-3 fatty acid which is a dietary precursor to eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). Stearidonic acid is present in small amounts in seed oils.

Suppliers44 total

陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]

艾吉析科技（上海）有限公司17717235263 · [email protected]

成都彼样生物科技有限公司18108052721 · [email protected]

广州佳途科技股份有限公司81960175 18933936954 · [email protected]

上海优宁维生物科技股份有限公司15921930842 15921930842 · [email protected]

Additional notes

DefinitionChEBI: An octadecatetraenoic acid having four double bonds located at positions 6, 9, 12 and 15 (the all-cis-isomer). It has been isolated from Lithospermum officinale and fish oils.