(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,9,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl benzoate

• ChemBase ID: 130570
• Molecular Formular: C31H38O11
• Molecular Mass: 586.62682
• Monoisotopic Mass: 586.24141204
• SMILES: CC1=C2[C@H](C(=O)[C@@]3([C@H](C[C@@H]4[C@]([C@H]3[C@@H]([C@@](C2(C)C)(C[C@@H]1O)O)OC(=O)c1ccccc1)(CO4)OC(=O)C)O)C)OC(=O)C
• Canonical SMILES: CC(=O)O[C@H]1C(=O)[C@]2(C)[C@@H](O)C[C@@H]3[C@]([C@H]2[C@@H]([C@]2(C(C1=C(C)[C@@H](O)C2)(C)C)O)OC(=O)c1ccccc1)(CO3)OC(=O)C
• InChI: InChI=1S/C31H38O11/c1-15-19(34)13-31(38)26(41-27(37)18-10-8-7-9-11-18)24-29(6,20(35)12-21-30(24,14-39-21)42-17(3)33)25(36)23(40-16(2)32)22(15)28(31,4)5/h7-11,19-21,23-24,26,34-35,38H,12-14H2,1-6H3/t19-,20-,21+,23+,24-,26-,29+,30-,31+/m0/s1
• InChIKey: OVMSOCFBDVBLFW-VHLOTGQHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,9,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^3,^1^0.0^4,^7]heptadec-13-en-2-yl benzoate
• IUPAC Traditional name: baccatin III
• Synonyms: Baccatin III; (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-Bis(acetyloxy)-12-(benzoyloxy)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-dodecahydro-4,9,11-trihydroxy-4a,8,13,13-tetramethyl-7,11-methano-5H-cyclodeca[3,4]benz[1,2-b]oxet-5-one; NSC 330753; Baccatin III; 巴卡丁 III

Database IDs

• CAS Number: 27548-93-2
• MDL Number: MFCD00153921
• PubChem SID: 24892055; 162224848
• PubChem CID: 65366

CALCULATED PROPERTIES

• Acid pKa: 9.661471
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 1.042699
• LogD (pH = 7.4): 1.0403587
• Log P: 1.0427289
• Molar Refractivity: 145.3486 cm^3
• Polarizability: 58.259655 Å^3
• Polar Surface Area: 165.89 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol; Methanol
• Apperance: Cryst.; White to Off-White Solid
• Melting Point: >206°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 45-46-22-36/37/38
• Safety Statements: 53-22-26-36/37/39-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H319-H335-H350
• GHS Precautionary statements: P201-P261-P305 + P351 + P338-P308 + P313
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95% (HPLC); 99.0

DETAILS

Sigma Aldrich - B8154

Application
紫杉酚的前体
包装
5 mg in glass bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. B8154.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - B101000

A precursor to Paclitaxel, a neoplasm inhibitor to ovarian and breast cancers found in Taxus species.

REFERENCES

• Katkovcinova, Z., et al.: J. Biosci., 63, 721 (2008)
• Tian, J., et al.: J. Pharm. Sci., 97, 3100 (2008)
• Miao, Z., et al.: App. Biochem. Microbiol., 45, 81 (2008)