9-Hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid

Base Information

• Chemical Name: 9-Hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
• CAS No.: 472-15-1
• Molecular Formula: C30H48O3
• Molecular Weight: 456.709
• Hs Code.: 29181985
• NSC Number: 113090
• Wikidata: Q104195794
• Mol file: 472-15-1.mol

Synonyms:9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid;Lup-20(29)-en-28-oic acid, 3.beta.-hydroxy-;38736-77-5;3-Epibetulinic acid;NSC113090;Lup-20(29)-en-28-oic acid, 3-hydroxy-, (3.beta.)-;SCHEMBL4143519;QGJZLNKBHJESQX-UHFFFAOYSA-N;BDBM512883;(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid;acs.jmedchem.1c00409_ST.478;BCP08998;AKOS025295351;NCI60_000293;3-Hydroxylup-20(29)-en-28-oic acid #;1H-Cyclopenta[a]chrysene, lup-20(29)-en-28-oic acid deriv.;Lupatic acid;Betulic acid;Mairin;ALS357;ALS 357;ALS-357

Chemical Property of 9-Hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid

Chemical Property:

• Appearance/Colour: powder
• Vapor Pressure: 2.67E-14mmHg at 25°C
• Melting Point: 295-298 °C (dec.)(lit.)
• Refractive Index: 7.8 ° (C=0.9, Pyridine)
• Boiling Point: 550 °C at 760 mmHg
• PKA: 4.61±0.70(Predicted)
• Flash Point: 300.5 °C
• PSA: 57.53000
• Density: 1.065 g/cm³
• LogP: 7.08950
• Storage Temp.: Store at +4°C
• Solubility.: Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).
• XLogP3: 8.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 456.36034539
• Heavy Atom Count: 33
• Complexity: 861

Purity/Quality:

99% ^*data from raw suppliers

Betulinic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

Useful:

• Canonical SMILES: CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)C(=O)O
• Description: Betulinic acid (472-15-1) is a natural Lupane triterpenoid from white birch tree (Betula pubescens). Induces apoptosis in a variety of cell lines.1 Induces mitochondrial permeability transition pore opening.2 ?Acts as a chemosensitizer for anticancer drug treatment in chemoresistant colon cancer cell lines.3 Cell permeable.
• Uses: antineoplastic Betulinic Acid is a natural pentacyclic triterpenoid. Betulinic Acid displays anti-inflammatory and anti-HIV activity. Betulinic Acid selectively induces apoptosis in tumor cells by directly activati ng the mitochondrial pathway of apoptosis through a p53- and CD95-independent mechanism. Betulinic Acid also exhibits TGR5 agonist activity Betulinic acid (BetA) has been used:to test its effects as an antiviral agent against Dengue virus (DENV)as a sterol regulatory element-binding protein (SREBP) inhibitor to repress the lipid metabolism and proliferation of clear cell renal cell carcinoma (ccRCC) cellsas a treatment to test its anti-tumor properties for cell viability and apoptotic cell death assays in multiple myeloma models

Technology Process of 9-Hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid

There total 33 articles about 9-Hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid 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: 96.3%

betulonic acid (4481-62-3) → Betulinic acid (472-15-1)

Guidance literature:

betulonic acid; With aluminum isopropoxide; benzyl alcohol; In tetrahydrofuran; at 65 ℃; for 2h;

With sodium hydroxide; In water; xylene; at 130 ℃; for 1h;

With acetic acid; In water; Conversion of starting material;

Reference yield: 94.0%

betulone (7020-34-0) → Betulinic acid (472-15-1)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; Acidic conditions;

DOI:10.1007/s10600-015-1442-1

Reference yield: 89.0%

betulin (473-98-3) → Betulinic acid (472-15-1)

Guidance literature:

betulin; With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; In acetic acid butyl ester; water; tert-butyl alcohol; at 20 ℃; for 6h;

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In acetic acid butyl ester; water; tert-butyl alcohol; Solvent; Concentration; Reagent/catalyst;

DOI:10.1039/c6gc02641a

upstream raw materials:

3-O-acetylbetulinic acid

lup-20(29)-en-28-oic-3-O-β-D-glucopyranosyl (2->1)-O-β-D-glucopyranoside

3β-trans-(3,4-dihydroxycinnamoyloxy)-20(29)-lupen-28-oic acid

α-L-rhamnopyranosyl-3β-hydroxy-lup-20(29)-en-28-oic acid

Downstream raw materials:

3-O-acetylbetulinic acid

3β-acetoxylup-20(29)-en-28-oic acid anhydride

dihydromethylbetulinate

Acetyl-dihydrobetulinsaeure-methylester

Refernces

• 1、 Ressmann, Anna K.,Kremsmayr, Thomas,Gaertner, Peter,Zirbs, Ronald,Bica, Katharina. "Toward a benign strategy for the manufacturing of betulinic acid". . p. 1014 - 1022. Retrieved 2017.
• 2、 Levdanskii,Levdanskii,Kuznetsov. "Sulfonation of Betulinic Acid by Sulfamic Acid". . p. 894 - 896. Retrieved 2015.
• 3、 Chatterjee, Parnali,Pezzuto, John M.,Kouzi, Samir A.. "Glucosidation of betulinic acid by Cunninghamella species". . p. 761 - 763. Retrieved 1999.
• 4、 Zhang, Xiao,Zou, Li-Hua,He, Yu-Lin,Peng, Cheng,Guo, Li,Xiong, Liang. "Triterpenoid saponins from the buds of Lonicera similis". . p. 2282 - 2290. Retrieved 2018.
• 5、 Koshkin, I. N.,Kulakov, I. V.,Vlasenko, V. S.. "The Effect of Experimental BCG Antigen–Betulin-Derived Conjugates on the Guinea Pig Immunological Response". . p. 837 - 844. Retrieved 2021/08/25.
• 6、 Chen, Yingying,Si, Longlong,Wang, Xinchen,Xiao, Sulong,Zhang, Bo,Zhang, Lihe,Zhang, Yongmin,Zhou, Demin,Zhu, Yinbiao. "Synthesis of a Hexavalent Betulinic Acid Derivative as a Hemagglutinin-Targeted Influenza Virus Entry Inhibitor". . p. 2546 - 2554. Retrieved 2020/08/14.