(1R,3R,8S,10R,13S,16S,17R)-8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.01,11.03,7.07,11.013,17]nonadecane-5,15,18-trione

Base Information

• Chemical Name: (1R,3R,8S,10R,13S,16S,17R)-8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.01,11.03,7.07,11.013,17]nonadecane-5,15,18-trione
• CAS No.: 15291-77-7
• Molecular Formula: C20H24O10
• Molecular Weight: 424.405
• Hs Code.: 29322090
• European Community (EC) Number: 604-876-0
• Wikidata: Q27077804
• Pharos Ligand ID: 3WQG7ZCWFP6B
• Metabolomics Workbench ID: 28675
• Mol file: 15291-77-7.mol

Synonyms:BN 52021;BN-52021;ginkgolide B;ginkgolide B, (1beta)-isomer;Ginkolide B

Chemical Property of (1R,3R,8S,10R,13S,16S,17R)-8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.01,11.03,7.07,11.013,17]nonadecane-5,15,18-trione

Chemical Property:

• Appearance/Colour: white crystal powder
• Melting Point: 280 °C (dec.)
• Boiling Point: 762.416 °C at 760 mmHg
• PKA: pKa1 7.14; pKa2 8.60; pKa3 11.89(at 25℃)
• Flash Point: 274.337 °C
• PSA: 148.82000
• Density: 1.645 g/cm³
• LogP: -1.36950
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO (up to 40 mg/ml) or in Ethanol (up to 10 mg/ml).
• Water Solubility.: Soluble in DMSO. Slightly soluble in water and ethanol
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 1
• Exact Mass: 424.13694696
• Heavy Atom Count: 30
• Complexity: 925

Purity/Quality:

more than 98% ^*data from raw suppliers

Ginkgolide B ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1C(=O)OC2C1(C34C(=O)OC5C3(C2O)C6(C(C5)C(C)(C)C)C(C(=O)OC6O4)O)O
• Isomeric SMILES: C[C@@H]1C(=O)O[C@@H]2[C@]1([C@@]34C(=O)O[C@H]5C3(C2O)C6([C@@H](C5)C(C)(C)C)[C@H](O4)OC(=O)C6O)O
• Description: Ginkgo biloba is a perennial tree belonging to Ginkgoaceae (Ginkgo biloba L., Yin Xing). Its seeds, also known as ginkgo, have a long history of application in traditional medicine for its medicinal value. With promoting blood circulation by removing blood stasis, Ginkgo biloba has a long history of its application in traditional Chinese medicineIn recent years, it has been widely used in the treatment of cerebral ischemic diseases. After further study, it was found that the effective component is ginkgolide compound, which laid the foundation for the development of small molecule drugs.
• Physical properties: Appearance: ginkgolide B is a white powder. Solubility: weighed 0.98?g and dissolves in 1L water (calculation). Melting point: the compound melts at 280? °C (calculation)
• Uses: Ginkgo (Ginkgo biloba) Plant Profile: bioactives, mechanism of action, references Ginkgolide B is used as a potent PAF-R antagonist. Ginkgolide B speeds up PAF hydrolysis by promoting PAF-AH I α2 homodimer activity. Additionally, this compound has been reported to inhibit neutrophil degranulation in vitro. Inhibits superoxide production in vitro and inhibits bronchoconstriction and is neuroprotective following oral administration in vivo.
• Indications: The injection consists of multiple components, and there are three kinds of substance mainly in diterpene ginkgolides meglumine injection. It promotes blood circulation by removing blood stasis and activates the channels and collaterals for cerebral ischemia treatment.
• Clinical Use: Oral and injection preparations are applied widely in clinical therapy. Made in oral preparation, flavonoids are the main component of raw material. There are little chemical compounds in injection, and ginkgolides are the main component whose content is different from each other. Listed ginkgolide injection is applied for ischemia stroke formed by blood stasis with promoting blood circulation by removing blood stasis and clearing and activating the channels and collaterals. Compared with Shuxuening injection in clinical trials, ginkgolides injection is consistent in improving indicators effect, such as protection in nerve injury and others.

Technology Process of (1R,3R,8S,10R,13S,16S,17R)-8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.01,11.03,7.07,11.013,17]nonadecane-5,15,18-trione

There total 34 articles about (1R,3R,8S,10R,13S,16S,17R)-8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.01,11.03,7.07,11.013,17]nonadecane-5,15,18-trione 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: 97.0%

α-benzylginkgolide B (170288-58-1) → ginkgolide B (15291-77-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 24h; under 2888 Torr;

DOI:10.1016/j.phytochem.2004.08.026

Reference yield: 89.0%

C26H38O10Si (112574-09-1) → (+/-)-ginkgolide (15291-77-7,112652-59-2,119322-54-2)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 23 ℃; for 14h;

DOI:10.1021/ja00210a083

Reference yield: 73.0%

1-O-(tert-Butyldiphenylsilyl)ginkgolid B (130523-06-7) → ginkgolide B (15291-77-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2h;

upstream raw materials:

1-O-(tert-Butyldiphenylsilyl)ginkgolid B

C₂₈H₃₂O₁₁

7-trifluoromethanesulfonyloxy-ginkgolide C

α-benzylginkgolide B

Downstream raw materials:

α-benzylginkgolide B

Refernces

• 1、 Jaracz, Stanislav,Malik, Shahid,Nakanishi, Koji. "Isolation of ginkgolides A, B, C, J and bilobalide from G. biloba extracts". . p. 2897 - 2902. Retrieved 2007/10/03.
• 2、 Weinges, Klaus,Schick, Hartmut. "Chemistry of Ginkgolides, IV. Synthesis of Ginkgolide B from Ginkgolide C". . p. 81 - 83. Retrieved 2007/10/02.