Betulin diacetate

Base Information

• Chemical Name: Betulin diacetate
• CAS No.: 1721-69-3
• Molecular Formula: C34H54O4
• Molecular Weight: 526.8
• European Community (EC) Number: 217-015-5
• NSC Number: 38876
• UNII: U2YW502S1Q
• DSSTox Substance ID: DTXSID701244307
• Nikkaji Number: J203.116G
• Wikidata: Q27290607
• Metabolomics Workbench ID: 132500
• ChEMBL ID: CHEMBL359080
• Mol file: 1721-69-3.mol

Synonyms:(+)-betulin;(+)-betulin diacetate;3,28-di-O-acetylbetulin;3,28-diacetoxy-betulin;betulin;betulin diacetate;betuline;betulinic alcohol;betulinol;betulinol biacetate;betulinol diacetate;lup-20(29)-en-3 alpha, 28,30-triol;lup-20(29)-ene-3 beta,28-diol;lup-20(29)-ene-3,28-diol, 3,28-diacetate, (3 beta)-;lup-20(29)-ene-3alpha,28-diol

Chemical Property of Betulin diacetate

Chemical Property:

• Vapor Pressure: 4.58E-12mmHg at 25°C
• Melting Point: 221-223 °C
• Refractive Index: 1.4662 (589.3 nm 227℃)
• Boiling Point: 548.089 °C at 760 mmHg
• Flash Point: 257.987 °C
• PSA: 52.60000
• Density: 1.062 g/cm³
• LogP: 8.13880
• Storage Temp.: 2-8°C
• XLogP3: 9.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 526.40221020
• Heavy Atom Count: 38
• Complexity: 998

Purity/Quality:

99%, ^*data from raw suppliers

BetulinDiacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)OC(=O)C)C)COC(=O)C
• Isomeric SMILES: CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)OC(=O)C)C)COC(=O)C
• Uses: Light stabilizer for cellulose and wood pulp. In manufacture of resins, laquers, emulsifiers and polyurethanes. Cosmetics additive.

Technology Process of Betulin diacetate

There total 37 articles about Betulin diacetate 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: 100.0%

betulin (473-98-3) + acetic anhydride (108-24-7) → betulin diacetate (1721-69-3)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 1h;

DOI:10.1016/j.bmc.2007.06.033

Reference yield: 98.0%

betulin (473-98-3) + 2,4,6,8-tetraacetyl-2,4,6,8-tetraazabicyclo<3,3,0>octan-3,7-dione (10543-60-9) → betulin diacetate (1721-69-3)

Guidance literature:

With trifluoroacetic acid; In chloroform; at 70 ℃; for 1h;

DOI:10.1007/s10600-019-02720-9

Reference yield: 88.0%

betulin (473-98-3) + acetyl chloride (75-36-5) → betulin diacetate (1721-69-3)

Guidance literature:

With silica gel HF-254/magnesium oxide; at 20 ℃; for 4.5h; chemoselective reaction; Green chemistry;

upstream raw materials:

betulin

acetic anhydride

2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide

28-acetoxybetulin

Downstream raw materials:

C₄₀H₆₀ClNO₃

(3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-(2-((tert-butoxycarbonyl)(4-chlorobenzyl)amino)-1-hydroxyethyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl acetate

(3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-(2-((tert-butoxycarbonyl)(4-chlorobenzyl)amino)acetyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl acetate

tert-butyl 4-chlorobenzyl(2-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-hydroxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-3a-yl)-2-oxoethyl)carbamate

Refernces

• 1、 Duchnik, Wiktoria,Günther, Andrzej,Klimowicz, Adam,Kucharski, ?ukasz,Makuch, Edyta,Nowak, Anna,Pe?ech, Robert. "Enhancement of the antioxidant and skin permeation properties of betulin and its derivatives". . . Retrieved 2021.
• 2、 Dischendorfer. "-". . . Retrieved 1923.
• 3、 Pettit et al.. "". . p. 2879,2882. Retrieved 1961.
• 4、 Santos, Rita C.,Salvador, Jorge A.R.,Marin, Silvia,Cascante, Marta,Moreira, Joao N.,Dinis, Teresa C.P.. "Synthesis and structure-activity relationship study of novel cytotoxic carbamate and N-acylheterocyclic bearing derivatives of betulin and betulinic acid". . p. 4385 - 4396. Retrieved 2010.
• 5、 Kazakova, Oxana B.,Medvedeva, Natalya I.,Tolstikov, Genrikh A.,Kukovinets, Olga S.,Yamansarov, Emil Y.,Spirikhin, Leonid V.,Gubaidullin, Aidar T.. "Synthesis of terminal acetylenes using POCl3 in pyridine as applied to natural triterpenoids". . p. 234 - 236. Retrieved 2010.
• 6、 Li, Jizhen,Goto, Masuo,Yang, Xiaoming,Morris-Natschke, Susan L.,Huang, Li,Chen, Chin-Ho,Lee, Kuo-Hsiung. "Fluorinated betulinic acid derivatives and evaluation of their anti-HIV activity". . p. 68 - 71. Retrieved 2016.
• 7、 Symon,Veselova,Kaplun,Vlasenkova,Fedorova,Lyutik,Gerasimova,Shvets. "Synthesis and antitumor activity of cyclopropane derivatives of betulinic and betulonic acids". . p. 286 - 291. Retrieved 2005.
• 8、 Kadela-Tomanek, Monika,B?benek, Ewa,Chrobak, Elwira,Marciniec, Krzysztof,Latocha, Ma?gorzata,Ku?mierz, Dariusz,Jastrz?bska, Maria,Boryczka, Stanis?aw. "Betulin-1,4-quinone hybrids: Synthesis, anticancer activity and molecular docking study with NQO1 enzyme". . p. 302 - 315. Retrieved 2019.
• 9、 Sun, I.-Chen,Wang, Hui-Kang,Kashiwada, Yoshiki,Shen, Jing-Kang,Cosentino, L. Mark,Chen, Chin-Ho,Yang, Li-Ming,Lee, Kuo-Hsiung. "Anti-AIDS agents. 34. Synthesis and structure-activity relationships of betulin derivatives as anti-HIV agents". . p. 4648 - 4657. Retrieved 1998.
• 10、 Ghosh, Pranab,Mandal, Amitava,Ghosh, Joydip,Pal, Chiranjib,Nanda, Ashis Kumar. "Synthesis of bioactive 28-hydroxy-3-oxolup-20(29)-en-30-al with antileukemic activity". . p. 141 - 153. Retrieved 2012.