8-Hydroxy-1-methyl-7-propan-2-yl-3,6,10,16-tetraoxaheptacyclo[11.7.0.02,4.02,9.05,7.09,11.014,18]icos-14(18)-en-17-one

Base Information

• Chemical Name: 8-Hydroxy-1-methyl-7-propan-2-yl-3,6,10,16-tetraoxaheptacyclo[11.7.0.02,4.02,9.05,7.09,11.014,18]icos-14(18)-en-17-one
• CAS No.: 38748-32-2
• Molecular Formula: C₂₀H₂₄O₆
• Molecular Weight: 360.407
• Hs Code.: 29321900
• European Community (EC) Number: 683-214-2
• DSSTox Substance ID: DTXSID90860559
• Wikipedia: Triptolide
• Wikidata: Q104977712
• Mol file: 38748-32-2.mol

Synonyms:38748-32-2;DTXSID90860559;(1S,2S,4S,5S,7R,8R,9S,11S,13S)-8-hydroxy-1-methyl-7-propan-2-yl-3,6,10,16-tetraoxaheptacyclo[11.7.0.0^{2,4.0^{2,9.0^{5,7.0^{9,11.0^{14,18]icos-14(18)-en-17-one;6-Hydroxy-8b-methyl-6a-(propan-2-yl)-3b,4,4a,6,6a,7a,7b,8b,9,10-decahydrotrisoxireno[6,7:8a,9:4b,5]phenanthro[1,2-c]furan-1(3H)-one

Chemical Property of 8-Hydroxy-1-methyl-7-propan-2-yl-3,6,10,16-tetraoxaheptacyclo[11.7.0.02,4.02,9.05,7.09,11.014,18]icos-14(18)-en-17-one

Chemical Property:

• Appearance/Colour: White crystalline solid
• Vapor Pressure: 5.51E-17mmHg at 25°C
• Melting Point: 226-227 °C
• Refractive Index: 1.647
• Boiling Point: 601.7 °C at 760 mmHg
• PKA: 14.25±0.60(Predicted)
• Flash Point: 220.7 °C
• PSA: 84.12000
• Density: 1.48 g/cm³
• LogP: 1.10310
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 360.15728848
• Heavy Atom Count: 26
• Complexity: 819

Purity/Quality:

95%-98% ^*data from raw suppliers

Triptolide ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)C12C(O1)C3C4(O3)C5(CCC6=C(C5CC7C4(C2O)O7)COC6=O)C
• Description: Triptolide (38748-32-2) possesses potent immunosuppressive and anti-inflammatory activity.? Irreversibly inhibits eukaryotic transcription via covalent binding to XPB, a subunit of the transcription factor TFIIH.1??Blocks transactivation of NFkB.2?Exhibits potent antiproliferative activity in 60 cancer cell lines (average IC50?= 12 nM) and synergizes with other anticancer agents.3?Inhibits the inflammatory response and remarkably decreases production of TNF-a, IL-1b and IL-6 in a rat model of rheumatoid arthritis.4
• Uses: Labelled Triptolite (T815600), diterpenoid triepoxide with immunosuppressant and antitumor properties. Triptolide is a diterpenoid triepoxide with immunosuppressant and antitumor properties.

Technology Process of 8-Hydroxy-1-methyl-7-propan-2-yl-3,6,10,16-tetraoxaheptacyclo[11.7.0.02,4.02,9.05,7.09,11.014,18]icos-14(18)-en-17-one

There total 18 articles about 8-Hydroxy-1-methyl-7-propan-2-yl-3,6,10,16-tetraoxaheptacyclo[11.7.0.02,4.02,9.05,7.09,11.014,18]icos-14(18)-en-17-one 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: 62.0%

l-triptonide (38647-11-9) → 14-epitriptolide (144539-79-7) + triptolide (38748-32-2,73414-46-7,73543-06-3,144539-79-7)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 20 ℃;

DOI:10.1016/j.bmcl.2005.12.098

Reference yield: 49.0%

l-triptonide (38647-11-9) → triptolide (38748-32-2,73414-46-7,73543-06-3,144539-79-7)

Guidance literature:

With sodium tetrahydroborate; Eu(fod)3; In methanol;

DOI:10.1021/jo9919613

Reference yield: 40.0%

(5bS,8S,8aR,9aS,9bS,10aR,10bS)-8-hydroxy-8a-isopropyl-10b-methyl-5,5b,6,8,8a,9a,9b,10b-octahydro-1H-bis(oxireno)[2',3':4b,5;2'',3'':6,7]phenanthro[1,2-c]furan-3(2H)-one → triptolide (38748-32-2,73414-46-7,73543-06-3,144539-79-7) + C20H24O6

Guidance literature:

With sodium phosphate dibasic dodecahydrate; 3-chloro-benzenecarboperoxoic acid; In benzene; at 20 ℃; for 96h;

DOI:10.1016/j.bmcl.2014.10.069

upstream raw materials:

l-triptonide

7β,14,19-trihydroxy-18(4->3)abeo-abieta-3,8,11,13-tetraen-18-oic acid lactone

(5R,6S,8R,9S)-3-Isopropyl-9-methyl-7,8,9,11,12,15-hexahydro-6H-16,20-dioxa-cyclopropa[5,6]cyclopenta[a]phenanthrene-4,17-dione

(3bR,9bS)-6-hydroxy-7-isopropyl-9b-methyl-3b,4,10,11-tetrahydrophenanthro[1,2-c]furan-1,5(3H,9bH)-dione

Downstream raw materials:

triptodiolide

16-hydroxytriptolide

5α-hydroxytriptolide

15-hydroxyltriptolide

Refernces

• 1、 Xu, Hongtao,Chen, Yi,Tang, Huanyu,Feng, Huijin,Li, Yuanchao. "Semisynthesis of triptolide analogues: Effect of B-ring substituents on cytotoxic activities". supporting information. p. 5671 - 5674. Retrieved 2015/01/08.
• 2、 Zhou, Bing,Li, Xiaomei,Feng, Huijin,Li, Yuanchao. "Efficient syntheis of the key intermediate triptophenolide methyl ether for the synthesis of(-)-triptolide". scheme or table. p. 5396 - 5401. Retrieved 2010/08/19.