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Betulin information


Betulin
Betulin
Names
IUPAC name
Lup-20(29)-ene-3β,28-diol
Systematic IUPAC name
(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
Other names
Betulinol, betuline, betulol, betulinic alcohol, trochol
Identifiers
CAS Number
  • 473-98-3 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
ChEMBL
  • ChEMBL23236 checkY
ChemSpider
  • 65272 checkY
ECHA InfoCard 100.006.797 Edit this at Wikidata
EC Number
  • 207-475-5
KEGG
  • C08618 checkY
PubChem CID
  • 72326
UNII
  • 6W70HN7X7O checkY
InChI
  • 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 checkY
    Key: FVWJYYTZTCVBKE-ROUWMTJPSA-N checkY
  • InChI=1/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
    Key: FVWJYYTZTCVBKE-ROUWMTJPBQ
SMILES
  • O[C@H]5CC[C@@]4([C@@H]3[C@@]([C@]2([C@@H]([C@@H]1[C@](CO)(CC[C@H]1C(=C)C)CC2)CC3)C)(C)CC[C@H]4C5(C)C)C
  • 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
Properties
Chemical formula
C30H50O2
Molar mass 442.728 g·mol−1
Appearance solid with needle-like crystals[1]
Melting point 256 to 257 °C (493 to 495 °F; 529 to 530 K)
Solubility in water
insoluble[1]
Solubility slightly soluble in ethanol and benzene; soluble in diethyl ether, ethyl acetate and ligroin[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Betulin is an abundant, naturally occurring triterpene. It is commonly isolated from the bark of birch trees. It forms up to 30% of the dry weight of silver birch bark.[2] It is also found in birch sap.[citation needed] Inonotus obliquus contains betulin.[3]

The compound in the bark gives the tree its white color which appears to protect the tree from mid-winter overheating by the sun. As a result, birches are some of the northernmost occurring deciduous trees.

  1. ^ a b c Haynes, William M.; Lide, David R.; Bruno, Thomas J. (2014). "3". CRC Handbook of Chemistry and Physics (95th ed.). Boca Raton, Florida: CRC Press. p. 340. ISBN 9781482208689. OCLC 908078665.
  2. ^ Green, Brian; Bentley, Michael D.; Chung, Bong Y.; Lynch, Nicholas G.; Jensen, Bruce L. (2007-12-01). "Isolation of Betulin and Rearrangement to Allobetulin. A Biomimetic Natural Product Synthesis". Journal of Chemical Education. 84 (12): 1985. Bibcode:2007JChEd..84.1985G. doi:10.1021/ed084p1985.
  3. ^ Gao, Yuan; Xu, Hongyu; Lu, Zhenming; Xu, Zhenghong (November 2009). "Quantitative determination of steroids in the fruiting bodies and submerged-cultured mycelia of Inonotus obliquus". Se Pu. 27 (6): 745–749. ISSN 1000-8713. PMID 20352924.

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Betulin

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Betulin is an abundant, naturally occurring triterpene. It is commonly isolated from the bark of birch trees. It forms up to 30% of the dry weight of...

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Birch bark tar

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tar in the archaeological record. The most characteristic molecules are betulin and lupeol, which are also present in birch bark. Some of these molecules...

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Hardwood

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Triterpenoids commonly purified from hardwoods include cycloartenol, betulin and squalene. Hardwood polyterpenes are rubber, gutta percha, gutta-balatá...

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Birch triterpenes

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g birch bark), including 84‑95 mg triterpenes calculated as the sum of betulin, betulinic acid, erythrodiol, lupeol, and oleanolic acid. It is thought...

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Alder

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tuberculosis. Recent clinical studies have verified that red alder contains betulin and lupeol, compounds shown to be effective against a variety of tumors...

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Birch sap

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glutamic acid, as well as minerals, enzymes, proteins, betulinic acid and betulin, antioxidants, sugar (fructose, glucose and small amounts of sucrose) and...

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Limonene

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Stigmasterol Tocopherols Cholesterol Testosterone Cholecalciferol Ecdysones Other Betulin Lanosterol Saponins Serratenediol Squalane Acids Oleanolic acid Ursolic...

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Euphorbia

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are largely caused by varying amounts of diterpenes. Triterpenes such as betulin and corresponding esters are other major components of the latex. In contact...

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Natural rubber

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Stigmasterol Tocopherols Cholesterol Testosterone Cholecalciferol Ecdysones Other Betulin Lanosterol Saponins Serratenediol Squalane Acids Oleanolic acid Ursolic...

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Birch

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fill the wound. Preliminary research indicates that the phytochemicals, betulin and possibly other triterpenes, are active in Episalvan gel and wound healing...

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Wood

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communic acid, mercusic acid and secodehydroabietic acid. Cycloartenol, betulin and squalene are triterpenoids purified from hardwood. Examples of wood...

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Steroid

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Birch bark

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substances of medicinal and chemical interest. Some of those products (such as betulin) also have fungicidal properties that help preserve bark artifacts, as...

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Dietary fiber

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Phyllodium pulchellum

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β-carbolines Seeds: Galactomannan, L-glucosyl rhamnoside of physcion Roots: Betulin, α-amyrin, β-sitosterol The alkaloids are mainly of three broad structural...

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Pseuderanthemum carruthersii

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1-hydroxysyringaresinol Pseuderesinol Pseuderanoside Squalene Oleanolic acid Lupeol Betulin Betulinic acid Pseuderanic acid "Pseuderanthemum carruthersii (Seem.) Guillaumin...

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Cholecalciferol

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Capsaicin

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Menthol

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Terpene

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Terpenoid

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Alnus rubra

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tuberculosis. Recent clinical studies have verified that red alder contains betulin and lupeol, compounds shown to be effective against a variety of tumors...

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Squalene

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Betula pendula

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fermented into a "wine". The outer part of the bark contains up to 20% betulin. The main components in the essential oil of the buds are α-copaene (~10%)...

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Pulp mill

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an extra loading for the chemical recovery system. Birchbark contains betulin, a terpenoid that easily creates deposits in a pulp mill. The earliest...

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Polyphenol

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Phytochemical

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Pehr von Afzelius

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medicarum lineæ primæ, (with Jacob Betulin) 1801. In reformandam pharmacopoeam Suecicam prolegomena, (with Jacob Betulin) 1801. Brevväxling mellan Christopher...

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Triterpene

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