(5Z,8Z,11Z,13E,15S)-15-hydroxyicosa-5,8,11,13-tetraenoic acid

• ChemBase ID: 133784
• Molecular Formular: C20H32O3
• Molecular Mass: 320.46628
• Monoisotopic Mass: 320.23514488
• SMILES: CCCCC[C@@H](/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O)O
• Canonical SMILES: CCCCC[C@@H](/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O)O
• InChI: InChI=1S/C20H32O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,17-14+/t19-/m0/s1
• InChIKey: JSFATNQSLKRBCI-VAEKSGALSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5Z,8Z,11Z,13E,15S)-15-hydroxyicosa-5,8,11,13-tetraenoic acid
• IUPAC Traditional name: 15 hete
• Synonyms: (15S,5Z,8Z,11Z,13E)-15-Hydroxyeicosatetraenoic acid; (S)-15-HETE; 15(S)-HETE; 15(S)-Hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid

Database IDs

• CAS Number: 54845-95-3
• MDL Number: MFCD00063590
• Beilstein Number: 2470466
• PubChem SID: 24895431; 162228061
• PubChem CID: 5280724

CALCULATED PROPERTIES

• Acid pKa: 4.8197722
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.594384
• LogD (pH = 7.4): 2.8212519
• Log P: 5.35636
• Molar Refractivity: 101.4695 cm^3
• Polarizability: 37.740055 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Flash Point: 14 °C; 57.2 °F

Safety Information

• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 1170
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-36/37/38
• Safety Statements: 7-16-26-36
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H315-H319-H335
• GHS Precautionary statements: P210-P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1170 3/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: ≥97.0% (HPLC)
• Concentration: ~150 μg/mL in ethanol
• Shipped in: dry ice

DETAILS

Sigma Aldrich - H1142

Biochem/physiol Actions
Metabolite of arachidonic acid via the 15-lipoxygenase pathway that may be involved in pulmonary anti-inflammatory responses through the inhibition of 5-lipoxygenase. 15(S)-HETE suppresses the incorporation of thymidine and biosynthesis of prostaglandin E2 in tumor cell cultures. Treatment of colon cancer cells with 15(S)-HETE inhibited cell proliferation and induced apoptosis, which was preceded by an increase in TGF-beta-inducible early gene (TIEG) and a decrease in Bcl-2.