(3S,4S)-3-ethyl-4-[(2S,4E,6R,8S,9R,10R)-9-hydroxy-4,6,8,10-tetramethyl-7-oxododec-4-en-2-yl]oxetan-2-one

• ChemBase ID: 133173
• Molecular Formular: C21H36O4
• Molecular Mass: 352.50814
• Monoisotopic Mass: 352.26135963
• SMILES: CC[C@H]1[C@@H](OC1=O)[C@@H](C)C/C(=C/[C@@H](C)C(=O)[C@@H](C)[C@@H]([C@H](C)CC)O)/C
• Canonical SMILES: CC[C@H]([C@H]([C@@H](C(=O)[C@@H](/C=C(/C[C@@H]([C@@H]1OC(=O)[C@H]1CC)C)\C)C)C)O)C
• InChI: InChI=1S/C21H36O4/c1-8-13(4)18(22)16(7)19(23)14(5)10-12(3)11-15(6)20-17(9-2)21(24)25-20/h10,13-18,20,22H,8-9,11H2,1-7H3/b12-10+/t13-,14-,15+,16+,17+,18-,20+/m1/s1
• InChIKey: UNBMQQNYLCPCHS-VYNDPHDASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4S)-3-ethyl-4-[(2S,4E,6R,8S,9R,10R)-9-hydroxy-4,6,8,10-tetramethyl-7-oxododec-4-en-2-yl]oxetan-2-one
• IUPAC Traditional name: (3S,4S)-3-ethyl-4-[(2S,4E,6R,8S,9R,10R)-9-hydroxy-4,6,8,10-tetramethyl-7-oxododec-4-en-2-yl]oxetan-2-one
• Synonyms: 2-Ethyl-3,11-dihydroxy-4,6,8,10,12-pentamethyl-9-oxo-6-tetradecenoic acid 1,3-lactone; Ebelactone B microbial

Database IDs

• CAS Number: 76808-15-6
• MDL Number: MFCD00036711
• PubChem SID: 162227450; 24894376
• PubChem CID: 6436821

CALCULATED PROPERTIES

• Acid pKa: 14.498025
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 5.0759892
• LogD (pH = 7.4): 5.0759892
• Log P: 5.0759892
• Molar Refractivity: 100.7281 cm^3
• Polarizability: 39.892128 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: RQ7720000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95% (HPLC)

DETAILS

Sigma Aldrich - E0886

Biochem/physiol Actions
Esterase (lipase) inhibitor. Also inhibits carboxypeptidase Y-like kininase that degrades bradykinin.1