Betulin

Base Information

• Chemical Name: Betulin
• CAS No.: 473-98-3
• Molecular Formula: C30H50O2
• Molecular Weight: 442.726
• Hs Code.: 29181985
• European Community (EC) Number: 207-475-5
• NSC Number: 692218
• UNII: 6W70HN7X7O
• DSSTox Substance ID: DTXSID101019934
• Nikkaji Number: J5.959E
• Wikipedia: Betulin
• Wikidata: Q419726
• Metabolomics Workbench ID: 28740
• ChEMBL ID: CHEMBL23236
• Mol file: 473-98-3.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

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 4.32E-13mmHg at 25°C
• Melting Point: 256-257 °C(lit.)
• Refractive Index: 1.524
• Boiling Point: 522.275 °C at 760mm Hg
• PKA: 15.10±0.10(Predicted)
• Flash Point: 210.873 °C
• PSA: 40.46000
• Density: 1.017 g/cm³
• LogP: 6.99720
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)
• XLogP3: 8.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 442.381080833
• Heavy Atom Count: 32
• Complexity: 786

Purity/Quality:

98% , ^*data from raw suppliers

Betulin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-20/21/22-68/20/21/22-68
• Safety Statements: 36/37-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)CO
• 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)O)C)CO
• Description: Sterol regulatory element binding protein 2 (SREBP-2) regulates cholesterol synthesis by activating the transcription of genes for HMG-CoA reductase and other enzymes of the cholesterol synthetic pathway. When cellular sterol levels are high, SREBP is bound by SCAP and Insig to ER membranes as a glycosylated precursor protein. Upon cholesterol depletion, the protein is cleaved to its active form and translocated into the nucleus to stimulate transcription of genes involved in the uptake and synthesis of cholesterol. Betulin, the precursor of betulinic acid, is a pentacyclic triterpene found in the bark of birch trees. Betulin inhibits the SREBP-driven pathway of cholesterol and fatty acid biosynthesis by promoting SCAP–Insig binding which prevents the activation and release of SREBP-2 from the ER. At 15-30 mg/kg/day, betulin has been shown to decrease lipid levels and increase insulin sensitivity in mice fed a western-type diet. In an atherosclerosis disease model, 30 mg/kg/day betulin can reduce the size and improve the stability of atherosclerotic plaques in LDLR-knockout mice. At 2.5-5 μg/ml betulin, in combination with cholesterol, demonstrates anticancer effects by inducing apoptosis in Jurkat cells, A549 lung carcinoma cells, and HeLa cervical carcinoma cells.
• Uses: antineoplastic, antihyperlipidemia birch bark extract is described as having anti-irritant and antiseptic properties, and effective in acne treatment. It is used to make sunburn products, soothing lotions, and aftershaves. The oil is astringent and is mainly used for its curative effects, especially in cases of acne and eczema. In folkloric medicine, birch bark extract was considered good for bathing skin eruptions. Destructive distillation of the bark’s white epidermis yields an empyreumatic oil known as oil of birch tar, Oleum rusci, or dagget. This is a thick, bituminous, brownish-black liquid with a pungent, balsamic odor. It contains a high percentage of methylsalicilate, creosol, and guaiacol and is almost identical to wintergreen oil. Betulin may be used in the preparation of betulinic acid, which shows anti-HIV, antimalarial and anti-inflammatory activities.

Technology Process of Betulin

There total 23 articles about Betulin 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: 96.0%

betulin diacetate (1721-69-3) → betulin (473-98-3)

Guidance literature:

With potassium hydroxide; In ethanol; for 2h; Heating;

Reference yield: 95.0%

3,28-bis(O-THP)-betulin → betulin (473-98-3)

Guidance literature:

With montmorillonite K-10; In methanol; at 40 - 50 ℃; for 2h;

DOI:10.1080/00397919908085755

Reference yield: 94.0%

betulin 3,28-bis-O-trifluoroacetate → betulin (473-98-3)

Guidance literature:

With sodium hydroxide; In ethanol; toluene; at 60 ℃; for 3h;

DOI:10.1134/S1070428010100088

upstream raw materials:

Betulinic acid

methyl betulinate

betulin diacetate

betulonic aldehyde

Downstream raw materials:

3,28-bis-(2-carboxy-benzoyloxy)-lup-20⁽²⁹⁾-ene

betulin diacetate

3,28-bis-benzoyloxy-lup-20⁽²⁹⁾-ene

betulin-28-yl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

Refernces

• 1、 Wang, Xia-Chang,Ouyang, Xiao-Wei,Hu, Li-Hong. "Three new lupane-type triterpenes from Ceriops tagal". . p. 576 - 581. Retrieved 2010.
• 2、 Ren, Yulin,Anaya-Eugenio, Gerardo D.,Czarnecki, Austin A.,Ninh, Tran Ngoc,Yuan, Chunhua,Chai, Hee-Byung,Soejarto, Djaja D.,Burdette, Joanna E.,de Blanco, Esperanza J. Carcache,Kinghorn, A. Douglas. "Cytotoxic and NF-κB and mitochondrial transmembrane potential inhibitory pentacyclic triterpenoids from Syzygium corticosum and their semi-synthetic derivatives". supporting information. p. 4452 - 4460. Retrieved 2018/07/31.
• 3、 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". experimental part. p. 141 - 153. Retrieved 2012/05/05.