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Details

Stereochemistry ABSOLUTE
Molecular Formula C30H50O2
Molecular Weight 442.7168
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BETULIN

SMILES

CC(=C)[C@@H]1CC[C@]2(CO)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12

InChI

InChIKey=FVWJYYTZTCVBKE-ROUWMTJPSA-N
InChI=1S/C30H50O2/c1-19(2)20-10-15-30(18-31)17-16-28(6)21(25(20)30)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h20-25,31-32H,1,8-18H2,2-7H3/t20-,21+,22-,23+,24-,25+,27-,28+,29+,30+/m0/s1

HIDE SMILES / InChI

Molecular Formula C30H50O2
Molecular Weight 442.7168
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 10 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Betulin is an extract from bark of the white birch tree, which has been known since the 18th century and is chemically defined. Betulin was discovered by German-Russian chemist Johann Tobias Lowitz. He was the first scientist to study and characterise betulin, and in doing was one of the first to isolate an active plant ingredient. In numerous scientific studies, the natural active ingredient betulin has been found to have anti-inflammatory, anti-bacterial and regenerating properties. Birken AG create a patented process for extracting high-quality betulin from birch bark. Betulin works as keratinocyte modulator and transient receptor potential channel stimulant. An extensive study program including three clinical phase III trials was initiated to develop the drug candidate Oleogel-S10, Betulin-based oleogel, as the lead indication for accelerated wound healing of partial thickness wounds. In addition, Oleogel-S10 obtained the Orphan Drug Designation for the treatment of hereditary skin disorder Epidermolysis bullosa (EB) from the European Commission. Betulin can be easily converted to betulinic acid, which possesses a wide spectrum of biological and pharmacological activities. Betulinic acid has antimalarial and anti-inflammatory activities. Betulinic acid and its derivatives have especially shown anti-HIV activity and cytotoxicity against a variety of tumor cell lines comparable to some clinically used drugs.

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.
1991 Jan-Feb
Potential anti-tumor promoting activity of lupane-type triterpenoids from the stem bark of Glochidion zeylanicum and Phyllanthus flexuosus.
2004 Dec
Lupane-triterpenes from Bupleurum flavum.
2005 Dec
Three new triterpenes from Nerium oleander and biological activity of the isolated compounds.
2005 Feb
Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with bis-sulfamates.
2005 Feb 1
Two diterpenes and three diterpene glucosides from Phlogacanthus curviflorus.
2005 Jan
Synthesis of phthalates of betulinic acid and betulin with cytotoxic activity.
2005 May 16
[Chemical constituents from the mangrove plant Ceriops tagal].
2005 Oct
Unusual naphthoquinones, catechin and triterpene from Byrsonima microphylla.
2005 Oct
Correlation of cytotoxic activity of betulinines and their hydroxy analogues.
2005 Oct 1
[Interferon-inducing properties of dry birch bark extract and its effect on experimental infection caused by hepatitis C virus].
2005 Sep-Oct
Protective effects of betulin and betulinic acid against ethanol-induced cytotoxicity in HepG2 cells.
2005 Sep-Oct
Chemical study of triterpenoid resinous materials in archaeological findings by means of direct exposure electron ionisation mass spectrometry and gas chromatography/mass spectrometry.
2006
[Antimycobacterial activity of a dry birch bark extract on a model of experimental pulmonary tuberculosis].
2006
Structure-activity relationships of triterpenoid saponins on fruiting body induction in Pleurotus ostreatus.
2006 Aug
Physical, chemical and pharmacological characterization of a new oleogel-forming triterpene extract from the outer bark of birch (betulae cortex).
2006 Dec
Streblus asper Lour. (Shakhotaka): A Review of its Chemical, Pharmacological and Ethnomedicinal Properties.
2006 Jun
Acyl-CoA: cholesterol acyltransferase inhibitors from Ilex macropoda.
2006 Mar
Protection of betulin against cadmium-induced apoptosis in hepatoma cells.
2006 Mar 1
Activity of lupane triterpenoids from Maytenus species as inhibitors of nitric oxide and prostaglandin E2.
2006 Mar 1
Glycosidation of lupane-type triterpenoids as potent in vitro cytotoxic agents.
2006 Oct 1
Pharmacological properties of the ubiquitous natural product betulin.
2006 Sep
Boc-lysinated-betulonic acid: a potent, anti-prostate cancer agent.
2006 Sep 15
Triterpenic and other lipophilic components from industrial cork byproducts.
2006 Sep 6
Reciprocal regulation of endothelial nitric-oxide synthase and NADPH oxidase by betulinic acid in human endothelial cells.
2007 Aug
A quantitative synthesis of the medicinal ethnobotany of the Malinké of Mali and the Asháninka of Peru, with a new theoretical framework.
2007 Dec 5
Simultaneous determination of betulin and betulinic acid in white birch bark using RP-HPLC.
2007 Feb 19
Phytochemical and antinociceptive properties of Matayba elaeagnoides Radlk. barks.
2007 Jul-Aug
Antimicrobial activity of oleanolic acid from Salvia officinalis and related compounds on vancomycin-resistant enterococci (VRE).
2007 Jun
In vitro evaluation of the cytotoxic and trypanocidal activities of Ampelozizyphus amazonicus (Rhamnaceae).
2007 May
Selective inhibition of the interaction of C1q with immunoglobulins and the classical pathway of complement activation by steroids and triterpenoids sulfates.
2007 May 15
Ethnobotanical remarks on Central and Southern Italy.
2007 May 30
[Effect of nitrogen-containing derivatives of the plant triterpenes betulin and glycyrrhetic acid on the growth of MT-4, MOLT-4, CEM, and Hep G2 tumor cells].
2007 Nov-Dec
Synthesis and structure-activity relationship study of cytotoxic germanicane- and lupane-type 3beta-O-monodesmosidic saponins starting from betulin.
2007 Sep 15
Betulin binds to melanocortin receptors and antagonizes alpha-melanocyte stimulating hormone induced cAMP generation in mouse melanoma cells.
2007 Sep-Oct
The use of primary hepatocytes from brown trout (Salmo trutta lacustris) and the fish cell lines RTH-149 and ZF-L for in vitro screening of (anti)estrogenic activity of wood extractives.
2008 Apr
An ethnobotanical study of medicinal plants in Mana Angetu district, southeastern Ethiopia.
2008 Apr 28
[Studies on chemical constituents from roots of Pterospermum heterophyllum].
2008 Aug
Effects of the wood extractives dehydroabietic acid and betulinol on reproductive physiology of zebrafish (Danio rerio)-a two-generation study.
2008 Feb 18
Tyrosinase inhibitors and sesquiterpene diglycosides from Guioa villosa.
2008 Jan
[Transformation of betulin diacetate by the Prins reaction].
2008 Jul-Aug
Investigation of Indian diospyros species for antiplasmodial properties.
2008 Jun
Synthesis of lupane-type saponins bearing mannosyl and 3,6-branched trimannosyl residues and their evaluation as anticancer agents.
2008 May 5
Identification of new molecules extracted from Quercus suber L. cork.
2008 Nov
Betulin binds to gamma-aminobutyric acid receptors and exerts anticonvulsant action in mice.
2008 Oct
Comparison with various parts of Broussonetia papyrifera as to the antinociceptive and anti-inflammatory activities in rodents.
2008 Sep
Efficacy and mechanism of action of KHBJ-9B, a new herbal medicine, and its major compound triterpenoids in human cartilage culture and in a rabbit model of collagenase-induced osteoarthritis.
2009 Feb
Anti-cancer effect of Betulin on a human lung cancer cell line: a pharmacoproteomic approach using 2 D SDS PAGE coupled with nano-HPLC tandem Mass Spectrometry.
2009 Feb
Treatment of actinic keratoses with a novel betulin-based oleogel. A prospective, randomized, comparative pilot study.
2009 Feb
Analysis of pentacyclic triterpenes by LC-MS. A comparative study between APCI and APPI.
2009 Jan
Patents

Patents

Sample Use Guides

In Vivo Use Guide
About 1 cm of Oleogel-S10 string (approximately 100 mg) per cm² (i.e. approximately 1 mm thick) was applied to one half of STSG donor site by applying it onto the wound-facing side of the wound dressing.
Route of Administration: Topical
In Vitro Use Guide
Betulin displayed a MIC of 12.5 ug/mL and an IC50 of 2.4 ug/mL against M. tuberculosis (H37Ra).
Substance Class Chemical
Created
by admin
on Tue Oct 22 15:41:26 UTC 2019
Edited
by admin
on Tue Oct 22 15:41:26 UTC 2019
Record UNII
6W70HN7X7O
Record Status Validated (UNII)
Record Version
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Name Type Language
BETULIN
INCI   MI  
INCI  
Official Name English
LUP-20(29)-ENE-3,28-DIOL, (3.BETA.)-
Common Name English
BETULINIC ALCOHOL
Common Name English
LUP-20(30)-ENE-3.BETA.,28-DIOL
Common Name English
(+)-BETULIN
Common Name English
BETULINE
Common Name English
BETULIN [MI]
Common Name English
CP BETULIN
Brand Name English
NSC-4644
Code English
LUP-20(29)-ENE-3.BETA.,28-DIOL
Common Name English
ORISTRACT BTL
Brand Name English
BETULIN [INCI]
Common Name English
BETULINOL
Common Name English
Code System Code Type Description
MERCK INDEX
M2462
Created by admin on Tue Oct 22 15:41:27 UTC 2019 , Edited by admin on Tue Oct 22 15:41:27 UTC 2019
PRIMARY Merck Index
PUBCHEM
72326
Created by admin on Tue Oct 22 15:41:27 UTC 2019 , Edited by admin on Tue Oct 22 15:41:27 UTC 2019
PRIMARY
CAS
473-98-3
Created by admin on Tue Oct 22 15:41:27 UTC 2019 , Edited by admin on Tue Oct 22 15:41:27 UTC 2019
PRIMARY
MESH
C002503
Created by admin on Tue Oct 22 15:41:27 UTC 2019 , Edited by admin on Tue Oct 22 15:41:27 UTC 2019
PRIMARY
WIKIPEDIA
Betulin
Created by admin on Tue Oct 22 15:41:27 UTC 2019 , Edited by admin on Tue Oct 22 15:41:27 UTC 2019
PRIMARY
ECHA (EC/EINECS)
207-475-5
Created by admin on Tue Oct 22 15:41:27 UTC 2019 , Edited by admin on Tue Oct 22 15:41:27 UTC 2019
PRIMARY