BETULIN

PRODUCT IDENTIFICATION
CAS NO. 473-98-3

BETULIN

EINECS NO. 207-475-5
FORMULA C30H50O2
MOL WT. 442.72

H.S. CODE

 2906.19.5000

TOXICITY

 

SYNONYMS Lup-20(30)-ene-3beta,28-diol; Trochol; Betuline; Betulinol; Betulol;

Lup-20(29)-ene-3beta,28-diol; Messagenin; Triterpenoid; Betulinic alcohol;

SMILES C1([C@@H]2CC[C@@]3([C@@]4([C@@H]([C@H]5[C@H](C(=C)C)CC [C@ @]5 (CC4)CO )CC[C@H]3[C@@]2(CC[C@@H]1O)C)C)C)(C)C

CLASSIFICATION

Triterpene

EXTRA NOTES

 Betulin (lup-20(29)-ene-3β,28-diol) is an abundant, naturally occurring triterpene. It is commonly isolated from the bark of birch trees and forms up to 30% of the dry weight of the extractive.[1] The purpose of the compound in the bark is not known. It can be converted to betulinic acid (the alcohol group replaced by a carboxylic acid group), which is biologically more active than betulin itself. (Wikipedia)

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE white crystalline powder
MELTING POINT 256 - 257 C (Sublimes)
BOILING POINT

 

SPECIFIC GRAVITY  
SOLUBILITY IN WATER Sparingly soluble
SOLVENT SOLUBILITY Sparingly soluble petroleum ether, carbon disulfide. One part is soluble in 149 parts alcohol, 251 ether, 113 chloroform, 417 benzene. Soluble in acetic acid.
pH  
VAPOR DENSITY

 

AUTOIGNITION

 

NFPA RATINGS

Health hazard: 2, Flammability: 0, Physical hazards: 0 

REFRACTIVE INDEX

  
FLASH POINT

 

STABILITY

Stable under ordinary conditions

EXTERNAL LINKS & GENERAL DESCRIPTION

Betulin is a constituent of the cork layer of the outer bark of Betula alba, B. pendula, B. pubescent and B. platyphylla. Other sources are Diospyros leucomelas, Nelumbo nucifera, Zizyphus mauritiana and seeds of Ziziphus vulgaris var. spinosus. Betulin also occurs as the palmitate in the glue firm bark of Trochodendron aralioides.The antiphlogistic activity of betulin was confirmed in various experimental models. Studies on the activity of a methanolic extract from the rhizomes of N. nucifera, as well as betulin and betulinic acid revealed a marked inhibition of the carrageenin- and serotonin-induced rat paw edema, which was comparable to that of the standard anti-inflammatory agents phenylbutazone and dexamethazone. The authors of these studies concluded that lupane derivatives (steroid triterpenes), have an affinity for glucocorticoid receptors. This mechanism of action was confirmed by another study on three triterpenes isolated from D. leucomelas: betulin, betulic acid (Recio et al. 1995) oleanolic (Singh et al. 1992) and ursolic acid (Najid et al. 1992). All triterpenes tested showed anti-inflammatory activity in the following model tests: serotonin -, cararrageenan-induced paw edema; and TPA- and EPP-induced eye edema. Administration of progesterone, actinomycine D and cycloheximide helped to clarify a glucocorticoidal mechanism of action for the compounds tested, and among which betulinic acid showed the highest activity (Recio et al. 1995). (http://www.zsf.jcu.cz/)

Betulinic acid is a pentacyclic triterpene. It has several botanical sources, but can also be chemically derived from betulin, a substance found in abundance in the outer bark of white birch trees (Betula alba). Betulinic acid has been found to selectively kill human melanoma cells while leaving healthy cells alive. For the past four decades, the incidence of melanoma has been increasing at a higher rate than any other type of cancer source:http://biotech.icmb.utexas.edu/)

Betulinic acid, a pentacyclic triterpene, is known to have inhibitory property for aminopeptidase N (EC 3.4.11.2) activity and thus is a potential anti-melanoma agent by selectively killing human melanoma cells. It is a chemical compounds that may assist in fighting oral bacteria which would promote tooth decay. It is also considered to have effective as a non-steroidal anti-inflammatory agent, antimalarial, and prostaglandin antagonist.

Expected Pharmacological Actions
  • Analgesic
  • Anti-HIV Agent
  • Anti-infective Agent
  • Anti-inflammatory Agent
  • Antimalarial
  • Antineoplastic Agent
  • Antiparasitic Agent
  • Antiprotozoal Agent
  • Antiretroviral Agent
  • Antirheumatic Agent
  • Antiviral Agent
  • Hormone Antagonist
  • Peripheral Nervous System Agent
  • Prostaglandin antagonist
  • Sensory System Agent
SALES SPECIFICATION

APPEARANCE

 white crystalline powder

ASSAY (G.C)

98.0% min

OPTICAL ROTATION

 +18.0° ~ +22.0° (c = 2 in pyridine)
MELTING POINT 256 - 257 C
TRANSPORTATION
PACKING
 
HAZARD CLASS  
UN NO. Not regulated
SAFETY INFORMATION

HAZARD OVERVIEW

May be harmful if swallowed. Causes mild skin irritation. Causes damage to organs. Toxic if inhaled. Causes respiratory tract irritation. Toxic if absorbed through skin. Causes skin irritation. Causes eye irritation. Toxic if swallowed.

GHS

 

SIGNAL WORD

Warning

PICTOGRAMS

HAZARD STATEMENTS

H303-H316-H370

P STATEMENTS

P260-P307 + P311

EC DIRECTIVES

 

HAZARD CODES

Xn

RISK PHRASES

20/21/22-68/20/21/22

SAFETY PHRASES

36/37