Tripdiolide

Base Information

• Chemical Name: Tripdiolide
• CAS No.: 38647-10-8
• Molecular Formula: C20H24O7
• Molecular Weight: 376.406
• Hs Code.: 2942000000
• NSC Number: 163063
• UNII: 7VRC678RTA
• DSSTox Substance ID: DTXSID401045708
• Nikkaji Number: J37.202A
• Wikipedia: Tripdiolide
• Wikidata: Q15634170
• ChEMBL ID: CHEMBL486403
• Mol file: 38647-10-8.mol

Synonyms:NSC-163063;tripdiolide

Chemical Property of Tripdiolide

Chemical Property:

• Vapor Pressure: 5.11E-20mmHg at 25°C
• Melting Point: 226-228 °C
• Refractive Index: 1.668
• Boiling Point: 656.4 °C at 760 mmHg
• PKA: 13.50±0.70(Predicted)
• Flash Point: 240.5 °C
• PSA: 104.35000
• Density: 1.56 g/cm³
• LogP: 0.07390
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 376.15220310
• Heavy Atom Count: 27
• Complexity: 851

Purity/Quality:

98%,99%, ^*data from raw suppliers

Tripdiolide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)C12C(O1)C3C4(O3)C5(CC(C6=C(C5CC7C4(C2O)O7)COC6=O)O)C
• Isomeric SMILES: CC(C)[C@@]12[C@@H](O1)[C@H]3[C@@]4(O3)[C@]5(C[C@@H](C6=C([C@@H]5C[C@H]7[C@]4([C@@H]2O)O7)COC6=O)O)C
• Uses: Tripdiolide is a potential anticancer agent and antiinflammatory agent from the plant Tripterygium wilfordii.

Technology Process of Tripdiolide

There total 20 articles about Tripdiolide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 47.0%

(7,8)β,(9,11)β,(12,13)α-tris(epoxy)-2β,19-dihydroxy-14-oxo-18(4->3)abeo-abieta-3-en-18-oic acid lactone → triptodiolide (38647-10-8) + C20H24O7

Guidance literature:

With methanol; sodium tetrahydroborate; tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III); at -78 ℃; for 1h;

DOI:10.1016/j.tet.2010.12.014

Reference yield: 18.0%

triptolide (38748-32-2,73414-46-7,73543-06-3,144539-79-7) → triptodiolide (38647-10-8) + 16-hydroxytriptolide (139713-80-7) + 5α-hydroxytriptolide (583028-68-6) + 1β-hydroxytriptolide

Guidance literature:

With Cunninghamella blakesleana; potato medium; In acetone; at 25 ℃; for 120h; Further byproducts given; Microbiological reaction;

DOI:10.1016/S0040-4020(03)00605-7

Reference yield:

14-methoxy-19-norabieta-4(18),8,11,13-tetraene (1229291-60-4) → triptodiolide (38647-10-8) + C20H24O7

Guidance literature:

Multi-step reaction with 19 steps

1.1: tert.-butylhydroperoxide; selenium(IV) oxide / dichloromethane; water / 20 °C

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.67 h / -78 °C / Inert atmosphere

2.2: 0.5 h / -78 °C / Inert atmosphere

3.1: tetrahydrofuran / 0.92 h / -30 °C / Inert atmosphere

4.1: potassium fluoride; water; dihydrogen peroxide; potassium hydrogencarbonate / tetrahydrofuran; methanol / 20 °C

5.1: pyridine / 3 h / 20 °C

6.1: pyridine; thionyl chloride / 8 h / 20 °C

7.1: water; potassium carbonate / methanol / 3 h / 20 °C

8.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 3 h / 20 °C

9.1: N-Bromosuccinimide; water / acetone / 4 h / 20 °C

10.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / tetrahydrofuran; water; tert-butyl alcohol / 3 h / 20 °C

11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C

12.1: ammonium cerium (IV) nitrate; water / acetonitrile / 5 h / 20 °C

13.1: dipyridinium dichromate / dichloromethane / 20 °C / Molecular sieve

14.1: boron tribromide / dichloromethane / 1 h / -78 °C / Inert atmosphere

14.2: 20 °C

15.1: methanol; sodium tetrahydroborate / 0.5 h / 0 °C

16.1: sodium periodate / methanol; water / 0.83 h / 0 °C

17.1: Oxone; 1,1,1-trifluoro-2-propanone; edetate disodium; sodium hydrogencarbonate / water; acetonitrile / 4 h / 0 - 25 °C / pH 7 - 7.5

18.1: dihydrogen peroxide; sodium hydroxide / methanol / 1 h / 25 °C

19.1: methanol; sodium tetrahydroborate; tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) / 1 h / -78 °C

With pyridine; methanol; tert.-butylhydroperoxide; selenium(IV) oxide; Oxone; potassium fluoride; sodium chlorite; sodium tetrahydroborate; sodium periodate; N-Bromosuccinimide; dipyridinium dichromate; thionyl chloride; ammonium cerium (IV) nitrate; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; oxalyl dichloride; tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III); 1,1,1-trifluoro-2-propanone; water; dihydrogen peroxide; edetate disodium; boron tribromide; sodium hydrogencarbonate; potassium carbonate; potassium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; acetone; acetonitrile; tert-butyl alcohol; 2.1: Swern oxidation / 2.2: Swern oxidation / 3.1: Grignard reaction / 8.1: Dess-Martin oxidation;

DOI:10.1016/j.tet.2010.12.014

upstream raw materials:

triptolide

14-methoxy-19-norabieta-4⁽¹⁸⁾,8,11,13-tetraene

(3bR,9bS,11S)-7-isopropyl-6-methoxy-11-(methoxymethoxy)-9b-methyl-3b,4,5,9b,10,11-hexahydrophenanthro[2,1-c]furan-1(3H)-one

(3bR,5r,9bS,11S)-5-hydroxy-7-isopropyl-6-methoxy-11-(methoxymethoxy)-9b-methyl-3b,4,5,9b,10,11-hexahydrophenanthro[2,1-c]furan-1(3H)-one

Refernces

• 1、 Ning, Lili,Zhan, Jixun,Qu, Guiqin,Zhong, Lei,Guo, Hongzhu,Bi, Kaishun,Guo, Dean. "Biotransformation of triptolide by Cunninghamella blakesleana". . p. 4209 - 4213. Retrieved 2007/10/03.