methyl 11-hydroxy-13-[(2S,3S)-3-pentyloxiran-2-yl]trideca-5,8,12-trienoate

• ChemBase ID: 153687
• Molecular Formular: C21H34O4
• Molecular Mass: 350.49226
• Monoisotopic Mass: 350.24570957
• SMILES: CCCCC[C@H]1[C@@H](O1)/C=C/C(C/C=C/C/C=C/CCCC(=O)OC)O
• Canonical SMILES: CCCCC[C@@H]1O[C@H]1/C=C/C(C/C=C/C/C=C/CCCC(=O)OC)O
• InChI: InChI=1S/C21H34O4/c1-3-4-10-14-19-20(25-19)17-16-18(22)13-11-8-6-5-7-9-12-15-21(23)24-2/h5,7-8,11,16-20,22H,3-4,6,9-10,12-15H2,1-2H3/t18?,19-,20-/m0/s1
• InChIKey: MHXSCMMMTRMMBI-YPJRHXLCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 11-hydroxy-13-[(2S,3S)-3-pentyloxiran-2-yl]trideca-5,8,12-trienoate
• IUPAC Traditional name: methyl 11-hydroxy-13-[(2S,3S)-3-pentyloxiran-2-yl]trideca-5,8,12-trienoate
• Synonyms: Methyl 14(S),15(S)-epoxy-11(R,S)-hydroxy-(5Z,8Z,12E)-eicosatrienoate

Database IDs

• EC Number: 203-777-6
• MDL Number: MFCD04040012
• PubChem SID: 162247826
• PubChem CID: 71311718

CALCULATED PROPERTIES

• Acid pKa: 14.834262
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.7201643
• LogD (pH = 7.4): 4.7201643
• Log P: 4.7201643
• Molar Refractivity: 104.4889 cm^3
• Polarizability: 40.029575 Å^3
• Polar Surface Area: 59.06 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: hexane solution
• Flash Point: -14.8 °F; -26 °C

Safety Information

• European Hazard Symbols: Flammable (F); Nature polluting (N); Harmful (Xn)
• UN Number: 1208
• German water hazard class: 2
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-38-48/20-51/53-62-65-67
• Safety Statements: 9-16-29-33-36/37-61-62
• GHS Pictograms: GHS02; GHS07; GHS08; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H304-H315-H336-H361f-H373-H411
• GHS Precautionary statements: P210-P261-P273-P281-P301 + P310-P331
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1208 3/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C21H34O4

DETAILS

Sigma Aldrich - M9190

Other Notes
15-Lipoxygenase product of arachidonic acid, formed by a similar biosynthesis as hepoxilins.
Application
Methyl 14(S),15(S)-epoxy-11(R,S)-hydroxy-(5Z,8Z,12E)-eicosatrienoate may be used as a reference material in the analysis and identification of 15-lipoxygenase metabolites.