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Betulin

Product Name:
Betulin
CAS No.
473-98-3
Chemical Name:
Betulin
CBNumber:
CB1301612
Molecular Formula:
C30H50O2
Formula Weight:
442.72
MOL File:
473-98-3.mol
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Betulin Property

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
form 
Off-white powder
pka
15.10±0.10(Predicted)
Merck 
14,1189
InChIKey
FVWJYYTZTCVBKE-ROUWMTJPSA-N
CAS DataBase Reference
473-98-3(CAS DataBase Reference)
NIST Chemistry Reference
Betulin(473-98-3)
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Safety

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
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N-Bromosuccinimide Price More Price(9)

Sigma-Aldrich Gold
Product number:
569371
Product name :
SREBP Processing Inhibitor, Betulin
Packaging:
250mg
Price:
$75.2
Updated:
2019/12/02
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Buy
Sigma-Aldrich Gold
Product number:
92648
Product name :
Betulin
Purity:
analytical standard
Packaging:
50mg
Price:
$119
Updated:
2019/12/02
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Buy
TCI Chemical Gold
Product number:
B0803
Product name :
Betulinol
Purity:
>97.0%(GC)
Packaging:
100mg
Price:
$63
Updated:
2020/06/24
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Buy
Cayman Chemical Gold
Product number:
11041
Product name :
Betulin
Purity:
≥98%
Packaging:
5g
Price:
$398
Updated:
2020/06/24
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Buy
Cayman Chemical Gold
Product number:
11041
Product name :
Betulin
Purity:
≥98%
Packaging:
1g
Price:
$90
Updated:
2020/06/24
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Betulin Chemical Properties,Usage,Production

Extract

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.
Betulin is a substance of pure plant origin that gives the birch bark its typical white colour. Betulin protects birch trees from environmental effects, such as extreme temperatures, pest infestations and solar radiation.

Physical and Chemical Properties

It is white crystalline powder, soluble in alcohol, chloroform and benzene, slightly soluble in cold water, petroleum ether.

Extraction method

Currently Betulin is obtained mainly through direct extraction, and mainly by solvent reflux extraction and recrystallization purification
Specifically:
1. Extract betulin from ethanol solution. After heating reflux about 5h, the extract is vacuum distillated and recrystallized with ethanol for 2 to 3 times with ethanol to obtain crude product of betulin.
2. The crude product was recrystallized from methanol/chloroform (1: 1) (every 80g crude product requires 300mL methanol/chloroform solution).The mixture is allowed to stand overnight and then suction filtered to obtain white needle-like betulin.
3. Ultrasonic treatment for 20min when refluxing is carried out, and the extraction yield and product purity of betulin can be improved through the destruction of bark organization.
4. The optimum conditions of supercritical CO2 fluid extraction are as follows: the amount of modifier was 115mL/(g birch bark powder); extraction pressure is 20MPa; extraction temperature was 55 ℃; liquid CO2 flow rate was 10kg/h.

Identification method

HPLC conditions for betulin:
Isolated Constituent: Betulin(10μl sample injection)
Column Stationary Phase: C18(150×2)mm 5μ
Column Mobile phase: Acetonitrile/water =30:70
Flow rate (ml/min);0.2Detection Wavelength (nm):270
Column Temperature:30℃

Physiological functions

  •  Betulin and its derivatives as biological agents has shown great potential in the treatment of HIV and cancer by interfering with the post-life cycle of the virus, which is related to the entry as well as growth and maturing of virus.
  •  As an effective anti-tumor drug, it can directly cause certain types of tumor cells to start self-destruction of the apoptosis program, and can slow down the growth of several types of tumor cells.
  • It can reduce dietary induced obesity, reduce lipid content in serum and tissue and improve insulin sensitivity.
  • It has mild anti-inflammatory properties at higher concentrations, and its anti-inflammatory properties are largely due to inhibition of non-neural gene pathways.
  • Betulin in the body can inhibit the maturation of sterol regulatory element binding protein (SBERPs), thereby reducing the biosynthesis of cholesterol and fatty acid.
  • In addition, with its anti-inflammatory, anti-virus effect and functions of inhibiting protein dissolution in the hair fiber, improving the luster of damaged hair and promoting hair growth and other activities, it can be used in food, cosmetics and pharmaceutical industries.

Storage

Cool and dry, kept from light and temperature.

References

http://www.imlan.de/en/infothek/what-is-betulin.html

Chemical Properties

crystals

Uses

antineoplastic, antihyperlipidemia

Uses

birch bark extract is described as having anti-irritant and antiseptic properties, and effective in acne treatment. It is used to make sunburn products, soothing lotions, and aftershaves. The oil is astringent and is mainly used for its curative effects, especially in cases of acne and eczema. In folkloric medicine, birch bark extract was considered good for bathing skin eruptions. Destructive distillation of the bark’s white epidermis yields an empyreumatic oil known as oil of birch tar, Oleum rusci, or dagget. This is a thick, bituminous, brownish-black liquid with a pungent, balsamic odor. It contains a high percentage of methylsalicilate, creosol, and guaiacol and is almost identical to wintergreen oil.

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.

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).

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Betulin Suppliers

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473-98-3, BetulinRelated Search:

Bengenin Resveratrol Rhynchophylline Lupeol ASTRAGALUS P.E. LUPANE betulin-(28)-5'-(aziridin-1-yl)-2',4'-dinitrobenzoate LUP-20(29)-EN-3,28-DIOL (BETULIN) betulin-(28)-5'-nitro-2'-furoate BETULIN(RG) Betulin-3-acetate,Betulin monoacetate Erythrodiol 3,28-di-O-(3',3'-dimethylglutaryl)betulin BETULIN(SH) 3-epi-Betulin BETULIN DIACETATE(RG),BETULIN DIACETATE LUP-20(29)-EN-3,28-DIOL, 3B-ACETATE LUP-20(29)-EN-3,28-DIOL, 28-ACETATE, (3B)
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  • 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
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  • Soluble BETULIN, Liposomal BETULIN, BETULIN NanoEmulsion, NanoActive BETULIN
  • Betulin 473-98-3
  • SREBP Processing Inhibitor, Betulin - CAS 473-98-3 - Calbiochem
  • 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
  • BETULINOL
  • 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
  • Birch bark extract
  • (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
  • TROCHOL
  • 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)
  • (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
  • BetuL
  • 473-98-3
  • Asymmetric Synthesis
  • Chiral Building Blocks
  • Complex Molecules
  • Triterpenoids
  • Tri-Terpenoids
  • natural product
  • Pentacyclic Triterpenes
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
Extract Physical and Chemical Properties Extraction method Identification method Physiological functions Storage References