Betulin

Structural formula
General
Surname	Betulin
other names	Betulinol; (+) - betulin; (3β) -Lup-20 (29) -en-3,28-diol; 3a-hydroxymethyl-1-isopropenyl-5a, 5b, 8,8,11a-pentamethyl-icosahydro-cyclopenta [a] chrysen-9-ol;
Molecular formula	C 30 H 50 O 2
Brief description	white solid
External identifiers / databases
EC number	207-475-5
ECHA InfoCard	100.006.797
PubChem	72326
Wikidata	Q419726
properties
Molar mass	442.72 g mol −1
Physical state	firmly
Melting point	257 ° C
solubility	almost insoluble in water
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 371
	P: 260
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Betulin is a naturally occurring chemical compound belonging to the group of pentacyclic triterpenes . These have a C30 body, the basic structure of which is based on five hydrocarbon rings. Four of them are six-rings, one a five-ring, which is the structural feature of the lupane group of substances .

history

The history of betulin goes back a long way. In 1788, the chemist Johann Tobias Lowitz discovered the substance and described it in the following words: “The small white flakes that appear on the white bark of the birch wood when it is brought close to an open fire and that evaporate from time to time , are a very nice, white, delicate vegetation, which I noticed only by chance, and then learned to collect them beautifully and often through practice. "

Occurrence and extraction

Bark of the paper birch

Pentacyclic triterpenes are widespread in the plant kingdom. The cork and bark of birch trees contain up to 40% pentacyclic triterpenes. Up to 34% of the dry matter of the white birch cork is accounted for by betulin, on average it is 22 percent. This makes betulin the main titerpene of the birch bark. Other components are the lupanes lupeol and betulinic acid as well as erythrodiol and oleanolic acid , which belong to the group of oleananes. Unlike the lupans, they have a basic structure consisting of five six-membered rings. In addition to birch cork, betulin is found in lower concentrations in the roots and leaves of the white ash ( Fraxinus americana ) and in the leaves and bark of the American mountain ash ( Sorbus americana ).

Betulin can easily be obtained by extraction from dry white birch bark.

properties

Betulin does not dissolve in water. It is readily soluble in chloroform. Betulin has anti-inflammatory properties.

use

Betulin is the main component of a birch bark extract, which was granted European approval as a drug for the treatment of dermal wounds in adults under the name Episalvan in 2016 . Betulin is also being investigated for the treatment of malaria , tumors and HIV .

Betulin is used as an emulsifying additive in shampoos .

Individual evidence

↑ ^a ^b ^c ^d Datasheet Betulin, ≥98% from Sigma-Aldrich , accessed on December 26, 2019 ( PDF ).

↑ David R. Lide: CRC Handbook of Chemistry and Physics A Ready-reference Book of Chemical and Physical Data . CRC Press, 1995, ISBN 978-0-8493-0595-5 , pp. 352 ( limited preview in Google Book search).

^ ^A ^b Johann Tobias Lowitz : About a new, almost benzoin-like substance of the birch trees. In: Lorenz Crell (Ed.): Chemische Annalen . for friends of the natural sciences, knowledge of Arzney, housekeeping and manufactories. tape 1788 , no. 1 . Fleckeisen / Müllersche Buchhandlung, Helmstädt and Leipzig 1788, OCLC 609930568 , p. 312–316 ( online at the Bayerische Staatsbibliothek digital): "several logs of young birch trees with white bark, erect, so close to a very quiet fire"

^ ^A ^b Brian Green, Michael D. Bentley, Bong Y. Chung, Nicholas G. Lynch, Bruce L. Jensen: Isolation of Betulin and Rearrangement to Allobetulin. A Biomimetic Natural Product Synthesis . In: Journal of Chemical Education . tape 84 , no. December 12 , 2007, pp. 1985 , doi : 10.1021 / ed084p1985 .

↑ ^a ^b S. Alakurtti, T. Mäkelä, S. Koskimies, J. Yli-Kauhaluoma: Pharmacological properties of the ubiquitous natural product betulin. In: European journal of pharmaceutical sciences: official journal of the European Federation for Pharmaceutical Sciences. Volume 29, Number 1, September 2006, pp. 1-13, doi : 10.1016 / j.ejps.2006.04.006 , PMID 16716572 .

↑ European Commission grants marketing authorization for Episalvan ( Memento of the original from January 25, 2016 in the Internet Archive ) Info: The archive link was automatically inserted and not yet checked. Please check the original and archive link according to the instructions and then remove this notice. , PM Birken AG of January 22, 2016

↑ SK Krol, M. Kiełbus, A. Rivero-Müller, A. Stepulak: Comprehensive review on betulin as a potent anticancer agent. In: BioMed research international. Volume 2015, 2015, p. 584189, doi : 10.1155 / 2015/584189 , PMID 25866796 , PMC 4383233 (free full text).

↑ SC Jonnalagadda, MA Corsello, CE Sleet: Betulin-betulinic acid natural product based analogs as anti-cancer agents. In: Anti-Cancer Agents in Medicinal Chemistry . Volume 13, Number 10, December 2013, pp. 1477-1499, PMID 23848199 .

^ Charles Gauthier, Jean Legault, Marianne Piochon-Gauthier, André Pichette: Advances in the synthesis and pharmacological activity of lupane-type triterpenoid saponins . In: Phytochemistry Reviews . tape 10 , no. 4 , December 2011, p. 521-544 , doi : 10.1007 / s11101-010-9176-y .

literature

Alakurtti, S., T. Makela, et al .: Pharmacological properties of the ubiquitous natural product betulin . In: European Journal of Pharmaceutical Sciences , 2006 . 29 : 1-13.
Ekman, R .: The Submarin monomers and triterpenoids from the outer bark of Betula verrucosa EHRH , In: Holzforschung , 1983 , 37 (4), pp. 205-211.
Gong, Y., KM Raj, et al .: The synergistic effects of betulin with acyclovir against herpes simplex viruses , In: Antiviral Research , 2004 , 64 (2), pp. 127-130.
Hayek, EWH, Jordis, U, Moche, W, Sauter, F .: A bicentennial of Betulin , In: Phytochemistry , 1989 , 28 (9), pp. 2229-2242.
Laszczyk, M., Jäger, S., et al .: Physical, chemical and pharmacological characterization of a new oleogel-forming triterpene extract from the outer bark of birch (betulae cortex) , In: Planta Medica , 2006 , 72 (15) , Pp. 1389-1395.
Oh, SH, JE Choi, et al .: Protection of betulin against cadmium-induced apoptosis in hepatoma cells , In: Toxicology , 2006 , 220 (1), pp. 1-12.
Reyes, CP, MJ Nunez, et al .: Activity of lupane triterpenoids from Maytenus species as inhibitors of nitric oxide and prostaglandin E2 , In: Bioorganic & Medicinal Chemistry , 2006 , 14 (5), pp. 1573-1579.
Entry on betulin. In: Römpp Online . Georg Thieme Verlag, accessed on January 3, 2015.
Weigenand, O., Hussein, AA, Lall, N. et al .: Antibacterial activity of Naphtoquinones and triterpenoids from euclea natalensis root bark , In: Journal of Natural Products , 2004 , 67 , pp. 1936-1938.

Web links

[Sigma-1] Datasheet Betulin, ≥98% from Sigma-Aldrich , accessed on December 26, 2019 ( PDF ).

[David_R._Lide-2] David R. Lide: CRC Handbook of Chemistry and Physics A Ready-reference Book of Chemical and Physical Data . CRC Press, 1995, ISBN 978-0-8493-0595-5 , pp. 352 ( limited preview in Google Book search).

[Lowitz-3] A ^b Johann Tobias Lowitz : About a new, almost benzoin-like substance of the birch trees. In: Lorenz Crell (Ed.): Chemische Annalen . for friends of the natural sciences, knowledge of Arzney, housekeeping and manufactories. tape 1788 , no. 1 . Fleckeisen / Müllersche Buchhandlung, Helmstädt and Leipzig 1788, OCLC 609930568 , p. 312–316 ( online at the Bayerische Staatsbibliothek digital): "several logs of young birch trees with white bark, erect, so close to a very quiet fire"