ChemicalBook > Product Catalog >Biochemical Engineering >Natural Products >Betulin

Betulin

Betulin Structure
CAS No.
473-98-3
Chemical Name:
Betulin
Synonyms
TROCHOL;Betuline;Birch bark extract;BETULINOL;betula camphor;(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(Hydroxymethyl)-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]chrysen-9-ol;BetuL;etulin;BETULIN;BETULOL
CBNumber:
CB1301612
Molecular Formula:
C30H50O2
Molecular Weight:
442.72
MOL File:
473-98-3.mol
MSDS File:
SDS
Modify Date:
2025/1/27 9:38:02

Betulin Properties

Melting point 256-257 °C(lit.)
alpha D15 +20° (c = 2 in pyridine)
Boiling point 493.26°C (rough estimate)
Density 0.9882 (rough estimate)
refractive index 1.5045 (estimate)
storage temp. 2-8°C
solubility Chloroform (Slightly), Methanol (Slightly, Heated)
form Off-white powder
pka 15.10±0.10(Predicted)
color Pale Brown to Beige
optical activity +2015 (c 6, pyridine)
Merck 14,1189
Stability Hygroscopic
InChIKey FVWJYYTZTCVBKE-ROUWMTJPSA-N
LogP 8.607 (est)
CAS DataBase Reference 473-98-3(CAS DataBase Reference)
NIST Chemistry Reference Betulin(473-98-3)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS08
Signal word  Warning
Hazard statements  H371
Precautionary statements  P260-P264-P270-P308+P311-P405-P501
Hazard Codes  Xn,Xi
Risk Statements  36/37/38-20/21/22-68/20/21/22-68
Safety Statements  36/37-36-26
WGK Germany  3
RTECS  OK5755000
HS Code  29181985
NFPA 704
0
2 0

Betulin price More Price(9)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) B9757 Betulin ≥98% 473-98-3 1G ₹17309.18 2022-06-14 Buy
Sigma-Aldrich(India) B9757 Betulin ≥98% 473-98-3 5G ₹35116.3 2022-06-14 Buy
Sigma-Aldrich(India) 92648 Betulin analytical standard 473-98-3 50MG ₹11864.2 2022-06-14 Buy
Sigma-Aldrich(India) 569371 SREBP Processing Inhibitor, Betulin - CAS 473-98-3 - Calbiochem The SREBP Processing Inhibitor, Betulin, also referenced under CAS 473-98-3, controls the biological activity of SCAP (SREBP cleavage activating prote 473-98-3 250MG ₹8310 2022-06-14 Buy
TCI Chemicals (India) B0803 Betulinol min. 97.0 % 473-98-3 100MG ₹7600 2022-05-26 Buy
Product number Packaging Price Buy
B9757 1G ₹17309.18 Buy
B9757 5G ₹35116.3 Buy
92648 50MG ₹11864.2 Buy
569371 250MG ₹8310 Buy
B0803 100MG ₹7600 Buy

Betulin Chemical Properties,Uses,Production

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.

Chemical Properties

crystals

Uses

Betulin may be used in the preparation of betulinic acid, which shows anti-HIV, antimalarial and anti-inflammatory activities.

Definition

ChEBI: A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-hydroxymethyl substituents.

General Description

A cell-permeable pentacyclic triterpenoid from birch bark extract that interacts with SCAP (SREBP cleavage activating protein) and prevents SREBP (sterol regulatory element-binding protein) Golgi proteolytic activation (1 to 13.55 μM in Rat hepatocytes CRL-1601) via a similar mechanism as oxysterols by inducing the association of SCAP with Insig-1 (insulin-induced gene-1), thereby causing SCAP-SREBPs complex ER retention. Unlike oxysterols, Betulin does not activate LXR to induce concomitant HMGCR (HMG-CoA reductase) degradation and SREBP-1 up-regulation. While both Betulin and HMGCR inhibitor Lovastatin (Cat. No. 438185) inhibit cellular cholesterol synthesis (by ~70% in CRL-1601 cultures with respective compound at 13.55 and 1 μM concentration), only Betulin suppresses cellular fatty acid synthesis (by ~55% at 13.55 μM in CRL-1601). Betulin is shown to exhibit comparable in vivo efficacy as Lovastatin (both dosed at 30 mg/kg/day with chow) in ameliorate high fat/cholesterol diet-induced obesity (% fat/lean tissue ratio increase from non-fat diet mice = 167, 44, and 33 in mice consuming fat diet alone, with Lovastatin, with Betulin, respectively). However, only Betulin is demonstrated to lower fasting blood glucose and insulin levels and reduce fat cell size in white adipose tissue in high fat diet mice. Fatostatin (Cat. No. 341329) in comparison does not target SCAP via sterol-binding site, nor does it induce SCAP binding to Insig-1.

Anticancer Research

In addition, triterpenoids (betulin and its derivatives) isolated from HSSEactivated the signaling pathway regulated by p53 family genes, leading to the inhibition of BC cell viability or even the induction of apoptosis. And also, theseresearchers found that all the triterpenoids had no effect on normal breast cells.These findings provide an important basis for the use of those triterpenoids in thedevelopment of alternative therapies for breast cancer treatment (Hsu et al. 2015).

Betulin Preparation Products And Raw materials

Global( 470)Suppliers
Supplier Tel Country ProdList Advantage Inquiry
GK Chemicals +91-7207279444 +91-7207279444 Hyderabad, India 340 58 Inquiry
CLEARSYNTH LABS LTD. +91-22-45045900 Hyderabad, India 6257 58 Inquiry
CHEMSWORTH +91-261-2397244 New Delhi, India 6700 30 Inquiry
Otto Chemie Pvt. Ltd. +91 9820041841 Mumbai, India 5870 58 Inquiry
TCI Chemicals (India) Pvt. Ltd. 1800 425 7889 New Delhi, India 6768 58 Inquiry
Pharmaffiliates Analytics and Synthetics P. Ltd +91-172-5066494 Haryana, India 6739 58 Inquiry
Pharma Affiliates 172-5066494 Haryana, India 6754 58 Inquiry
Natucare India 08048372644Ext 102 Mumbai, India 8 58 Inquiry
Biopharmacule Speciality Chemicals P Ltd (India) +91 40 6462 1866 Hyderabad, India 526 58 Inquiry
Hovane Phytochemicals Co., Ltd +86-17340288373 China 33 58 Inquiry

Related articles

Lup-20(29)-ene-3,28-diol, (3β)- BETULIN(P) BETULIN hplc Betulin,Betulinol,Betulol,Betulenol 3b,28-Dihydroxylup-20(29)-ene Betulinic alcohol SpirulinaPowder&Tablets etulin BETULIN WITH HPLC Betulin(98%) NSC 4644 (1R,3AS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(Hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-(pr SREBP Processing Inhibitor, Betulin Lup-2(29)-ene-3b,28-diol Lup-20(30)-ene-3b,28-diol 5α-Lupan-20(29)-ene-3β,28-diol Lupane-20(29)-ene-3β,28-diol (1R,3AS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(Hydroxymethyl)-5a,5b,8,8,1 1a-pentamethyl-1-(prop BETULIN BETULOL LUP-20(29)-ENE-3,28-DIOL,(3B) LUP-20[29]-ENE3B,28-DIOL LUP-20(29)-ENE-3BETA,28-DIOL LUP-20(29)-EN-3,28-DIOL (1R,2R,5S,8R,9R,10R,13R,14R,17S,19R)-5-(hydroxyMethyl)-1,2,14,18,18-pentaMethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-17-ol Betulinol (obsol 28-diol Lup-20(29)-ene-3b (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxyMethyl)-5a,5b,8,8,11a-pentaMethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-ol lup-20(29)-ene-3,28-diol Lup-20(29)-ene-3,28-diol, (3beta)- BETULIN CRYSTALLINE BETULIN: LUP-20(29)-ENE-3,28-DIOL,(3B) Betulinol > BetuL (3aS,5bR,9S,11aR)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-(1-methylethenyl)-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol SREBP Processing Inhibitor, Betulin - CAS 473-98-3 - Calbiochem Betulin 473-98-3 Soluble BETULIN, Liposomal BETULIN, BETULIN NanoEmulsion, NanoActive BETULIN Betuline betula camphor (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(Hydroxymethyl)-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]chrysen-9-ol BETULINOL Birch bark extract TROCHOL Betulin alcohol Betulin in diisopropyl ether Betulin-RM 473-98-3 Asymmetric Synthesis Chiral Building Blocks Complex Molecules Triterpenoids Tri-Terpenoids natural product Pentacyclic Triterpenes chemical reagent pharmaceutical intermediate