Ormosin VI
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MedKoo CAT#: 465407

CAS#: 78454-17-8

Description: Ormosin VI is a taxane diterpenoid and derivative of paclitaxe that has been found in Taxus and has α-glucosidase inhibitory and anticancer activities. It inhibits α-glucosidase (IC50 = 48.8 µM) and is cytotoxic to HeLa cells (IC50 = 0.085 nM). Ormosin VI induces apoptosis and DNA fragmentation in HepG2 hepatocellular carcinoma cells in a concentration-dependent manner.


Chemical Structure

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Ormosin VI
CAS# 78454-17-8

Theoretical Analysis

MedKoo Cat#: 465407
Name: Ormosin VI
CAS#: 78454-17-8
Chemical Formula: C45H49NO13
Exact Mass: 811.3204
Molecular Weight: 811.881
Elemental Analysis: C, 66.57; H, 6.08; N, 1.73; O, 25.62

Price and Availability

Size Price Availability Quantity
1.0mg USD 280.0 2 Weeks
5.0mg USD 540.0 2 Weeks
10.0mg USD 900.0 2 Weeks
25.0mg USD 1640.0 2 Weeks
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Synonym: Ormosin VI; 10-Deacetyl-7-epitaxol; 10-Deacetyl-7-epi-paclitaxel; 10-Deacetyl-7-epipaclitaxel; 10-Desacetyl-7-epi-taxol; 10-Desacetyl-7-epipaclitaxel; 7-epi-10-deacetyl Paclitaxel; 7-epi-10-Deacetyltaxol;

IUPAC/Chemical Name: (2aR,4R,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-9-(((2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl)oxy)-4,6,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate

InChi Key: TYLVGQKNNUHXIP-DIYBZAJCSA-N

InChi Code: InChI=1S/C45H49NO13/c1-24-29(57-41(54)35(50)33(26-15-9-6-10-16-26)46-39(52)27-17-11-7-12-18-27)22-45(55)38(58-40(53)28-19-13-8-14-20-28)36-43(5,37(51)34(49)32(24)42(45,3)4)30(48)21-31-44(36,23-56-31)59-25(2)47/h6-20,29-31,33-36,38,48-50,55H,21-23H2,1-5H3,(H,46,52)/t29-,30+,31+,33-,34+,35+,36-,38-,43+,44-,45+/m0/s1

SMILES Code: C[C@@]1([C@@]([H])([C@@](CO2)(OC(C)=O)[C@]2(C[C@H]1O)[H])[C@@H]3OC(C4=CC=CC=C4)=O)C([C@H](O)C5=C([C@H](C[C@@]3(C5(C)C)O)OC([C@@H]([C@@H](NC(C6=CC=CC=C6)=O)C7=CC=CC=C7)O)=O)C)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 10.0 12.32
DMSO 5.0 6.16

Preparing Stock Solutions

The following data is based on the product molecular weight 811.881 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Fathima JS, Selvaraj J, Sivabalan V, Rekha UV, Ponnulakshmi R, Vishnupriya V, Kullappan M, Sreekandan RN, Mohan SK, Vijayalakshmi P. Molecular docking of potential inhibitors with the mTOR protein. Bioinformation. 2021 Jan 31;17(1):212-217. doi: 10.6026/97320630017212. PMID: 34393439; PMCID: PMC8340694.

2: Subban K, Singh S, Subramani R, Johnpaul M, Chelliah J. Fungal 7-epi-10-deacetyltaxol produced by an endophytic Pestalotiopsis microspora induces apoptosis in human hepatocellular carcinoma cell line (HepG2). BMC Complement Altern Med. 2017 Nov 28;17(1):504. doi: 10.1186/s12906-017-1993-8. PMID: 29183320; PMCID: PMC5706334.

3: Dang PH, Nguyen HX, Duong TTT, Tran TKT, Nguyen PT, Vu TKT, Vuong HC, Phan NHT, Nguyen MTT, Nguyen NT, Awale S. α-Glucosidase Inhibitory and Cytotoxic Taxane Diterpenoids from the Stem Bark of Taxus wallichiana. J Nat Prod. 2017 Apr 28;80(4):1087-1095. doi: 10.1021/acs.jnatprod.7b00006. Epub 2017 Feb 27. Erratum in: J Nat Prod. 2017 Jul 28;80(7):2188. PMID: 28240909.

4: Fu YJ, Sun R, Zu YG, Li SM, Liu W, Efferth T, Gu CB, Zhang L, Luo H. Simultaneous determination of main taxoids in Taxus needles extracts by solid- phase extraction-high-performance liquid chromatography with pentafluorophenyl column. Biomed Chromatogr. 2009 Jan;23(1):63-70. doi: 10.1002/bmc.1085. PMID: 18816506.

5: Tian J, Stella VJ. Degradation of paclitaxel and related compounds in aqueous solutions II: Nonepimerization degradation under neutral to basic pH conditions. J Pharm Sci. 2008 Aug;97(8):3100-8. doi: 10.1002/jps.21214. PMID: 17963215.

6: Tian J, Stella VJ. Degradation of paclitaxel and related compounds in aqueous solutions I: epimerization. J Pharm Sci. 2008 Mar;97(3):1224-35. doi: 10.1002/jps.21112. PMID: 17680660.

7: Cao X, Tian Y, Zhang TY, Ito Y. Semi-preparative separation and purification of taxol analogs by high-speed countercurrent chromatography. Prep Biochem Biotechnol. 1998 Feb;28(1):79-87. doi: 10.1080/10826069808010128. PMID: 9516644.

8: Zobel AM, Furmanowa M, Glowniak K, Cragg C. Taxol on the surface of leaves and inside the needles of three species and two varieties of Taxus. Phytomedicine. 1996 Nov;3(3):287-91. doi: 10.1016/S0944-7113(96)80068-7. PMID: 23195085.

9: Ellis DD, Zeldin EL, Brodhagen M, Russin WA, McCown BH. Taxol production in nodule cultures of Taxus. J Nat Prod. 1996 Mar;59(3):246-50. doi: 10.1021/np960104g. PMID: 8882426.

10: Kitagawa I, Mahmud T, Kobayashi M, Roemantyo, Shibuya H. Taxol and its related taxoids from the needles of Taxus sumatrana. Chem Pharm Bull (Tokyo). 1995 Feb;43(2):365-7. doi: 10.1248/cpb.43.365. PMID: 7728941.