GARCINOLIC ACID; TRANS-(SH)

Base Information

• Chemical Name: GARCINOLIC ACID; TRANS-(SH)
• CAS No.: 91893-83-3
• Molecular Formula: C₂₇H₃₈O₄
• Molecular Weight: 426.596
• Mol file: 91893-83-3.mol

Synonyms:GARCINOLIC ACID; TRANS-(SH);Garcinoic acid

Chemical Property of GARCINOLIC ACID; TRANS-(SH)

Chemical Property:

• Storage Temp.: ?20°C

Purity/Quality:

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

Garcinoic acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T,N
• Statements: 25-50
• Safety Statements: 61

MSDS Files:

Useful:

• Description: Garcinoic acid is a derivative of vitamin E originally isolated from C. grandiflora. It inhibits IL-1β-induced microsomal prostaglandin E2 synthase-1 (mPGES-1) activity in A549 cells when used at concentrations of 1 and 10 μM. It has higher antioxidant activity relative to (±)-α-tocopherol in a cell-free assay when used at a concentration of 0.15 mM.
• Uses: Garcinoic Acid displays anti-angiogenic activity as well as anti-oxidative activity in animals.

Technology Process of GARCINOLIC ACID; TRANS-(SH)

There total 26 articles about GARCINOLIC ACID; TRANS-(SH) 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: 90.0%

(2E,6E,10E)-ethyl 13-((R)-6-hydroxy-2,8-dimethyl-2H-chroman-2-yl)-2,6,10-rimethyltrideca-2,6,10-trienoate (866468-10-2) → Garcinoic acid (91893-83-3)

Guidance literature:

With lithium hydroxide; water; In tetrahydrofuran; methanol; at 40 ℃; for 12h;

DOI:10.1021/ol051849t

Reference yield:

(4E,8E)-9-iodo-4,8-dimethylnona-4,8-dienal (866468-07-7) → Garcinoic acid (91893-83-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 85 percent / toluene / 0.5 h / 90 °C

2: 81 percent / t-BuLi; 9-MeO-9-BBN; K₃PO₄ / Pd(dppf)Cl₂; DMF / diethyl ether; hexane; pentane / 2 h / 20 °C

3: 92 percent / TBAF / tetrahydrofuran / 0 - 20 °C

4: 96 percent / CAN; H₂O / tetrahydrofuran / 0.58 h / 0 °C

5: methylhydroquinone; TsOH / benzene / 0.33 h / 80 °C

6: 90 percent / LiOH; H₂O / methanol; tetrahydrofuran / 12 h / 40 °C

With lithium hydroxide; potassium phosphate; ammonium cerium(IV) nitrate; 2-methylbenzene-1,4-diol; tetrabutyl ammonium fluoride; water; tert.-butyl lithium; toluene-4-sulfonic acid; 9-methoxy-9-BBN; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; diethyl ether; hexane; toluene; pentane; benzene; 1: Wittig reaction / 2: Suzuki coupling;

DOI:10.1021/ol051849t

Reference yield:

(E)-4-(2,5-dimethoxy-3-methylphenyl)but-3-en-2-one (866468-12-4) → Garcinoic acid (91893-83-3)

Guidance literature:

Multi-step reaction with 13 steps

1: 99 percent / H₂; KOAc / Pd(OH)2/C / ethyl acetate / 1 h

2: 96 percent / NaH / tetrahydrofuran / 0 - 20 °C

3: 93 percent / DIBAL-H / tetrahydrofuran / 1 h / 0 °C

4: Ti(O-i-Pr)4; (+)-diethyl tartrate; 4 Angstroem molecular sieves / tert-butyl hydroperoxide / CH₂Cl₂ / 1.5 h / -20 °C

5: 0.48 g / Red-Al / tetrahydrofuran; toluene / 0 - 20 °C

6: 85 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

7: 96 percent / NaI / acetone / 5 h / Heating

8: 91 percent / 4 Angstroem molecular sieves; 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

9: 81 percent / t-BuLi; 9-MeO-9-BBN; K₃PO₄ / Pd(dppf)Cl₂; DMF / diethyl ether; hexane; pentane / 2 h / 20 °C

10: 92 percent / TBAF / tetrahydrofuran / 0 - 20 °C

11: 96 percent / CAN; H₂O / tetrahydrofuran / 0.58 h / 0 °C

12: methylhydroquinone; TsOH / benzene / 0.33 h / 80 °C

13: 90 percent / LiOH; H₂O / methanol; tetrahydrofuran / 12 h / 40 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; lithium hydroxide; potassium phosphate; ammonium cerium(IV) nitrate; 4 A molecular sieve; 2-methylbenzene-1,4-diol; tetrabutyl ammonium fluoride; water; hydrogen; tert.-butyl lithium; potassium acetate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; (+)-Weinsaeure-diethylester; triethylamine; 9-methoxy-9-BBN; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium iodide; tert.-butylhydroperoxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium dihydroxide; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate; acetone; toluene; pentane; benzene; 2: Horner-Emmons olefination / 4: Sharpless epoxidation / 9: Suzuki coupling;

DOI:10.1021/ol051849t

upstream raw materials:

(2E,6E,10E)-ethyl 13-((R)-6-hydroxy-2,8-dimethyl-2H-chroman-2-yl)-2,6,10-rimethyltrideca-2,6,10-trienoate

(4E,8E)-9-iodo-4,8-dimethylnona-4,8-dienal

(E)-4-(2,5-dimethoxy-3-methylphenyl)but-3-en-2-one

(4E,8E)-9-iodo-4,8-dimethylnona-4,8-dien-1-ol