[CAS NO. 473-98-3] Betulin

Name: Betulin
Brand: Arctom Scientific
SKU: SLK-S4754

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PRODUCTS SPECIFICATIONS [473-98-3]

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Catalog

SLK-S4754

Brand

Selleck

CAS

473-98-3

DESCRIPTION [473-98-3]

Overview

MDL	-
Molecular Weight	442.72
Molecular Formula	C30H50O2
SMILES	C(O)[C@]12[C@@]([C@@]3([C@](C)([C@@]4(C)[C@](CC3)([C@]5(C)[C@@](CC4)(C(C)(C)[C@@H](O)CC5)[H])[H])CC1)[H])([C@H](C(C)=C)CC2)[H]

For research use only.

Storage

3 years,-20°C,powder
1 years,-80°C,in solvent

Shipping

Room temperature shipping(Stability testing shows this product can be shipped without any cooling measures.)

Preparing Stock Solutions

Concentration Volume Mass	1 mg	5 mg	10 mg
1 mM	2.2588 mL	11.2938 mL	22.5876 mL
5 mM	0.4518 mL	2.2588 mL	4.5175 mL
10 mM	0.2259 mL	1.1294 mL	2.2588 mL
50 mM	-	-	-

Description

Betulin (BE, betulinol, betuline, betulinic alcohol), also known as betulinol, betuline, or betulinic alcohol, is a pentacyclic lupane-type triterpenoid naturally distributed in many plants and displays a broad spectrum of biological and pharmacological properties such as anticancer and chemopreventive activity. Betulin (Trochol), is a sterol regulatory element-binding protein (SREBP) inhibitor with an IC50 of 14.5 μM in K562 cell line.

In vitro

Betulin significantly inhibits cell viability in cervix carcinoma HeLa cells, hepatoma HepG2 cells, lung adenocarcinoma A549 cells, and breast cancer MCF-7 cells with IC50 values ranging from 10 to 15 mg/mL. While betulin exhibits only moderate anticancer activity in other human cancer cells such as hepatoma SK-HEP-1 cells, prostate carcinoma PC-3, and lung carcinoma NCI-H460, with IC50 values ranging from 20 to 60 mg/mL, it shows minor growth inhibition in human erythroleukemia K562 cells (IC50>100 mg/mL). Betulin does not directly trigger mitochondrial cytochrome c release in isolated mitochondria. Bax and Bak are rapidly translocated to the mitochondria 30 min after betulin treatment. In vitro, Betulin inhibits LPS-induced tumor necrosis factor α (TNF-α) and (interleukin) IL-6 levels and up-regulates the level of IL-10. Also Betulin suppresses the phosphorylation of nuclear factor-kB (NF-kB) p65 protein in LPS-stimulated RAW 264.7 cells.

In vivo

In vivo, Betulin alleviates LPS-induced acute lung injury. Treatment with Betulin diminishes pro-inflammatory cytokines, myeloperoxidase activity and bacterial loads in lung tissue during gramnegative pneumonia. In HFD-fed apoE mice, betulin administration significantly reduces lesions in en face aortas and aortic sinuses. Furthermore, betulin administration significantly increases ABCA1 expression and suppresses macrophage positive areas in the aortic sinuses. Moreover, betulin administration improves plasma lipid profiles and enhances fecal cholesterol excretion in the mice.

References

[1] Li Y, et al. Mol Carcinog. 2010, 49(7):630-40.
[2] Wu Q, et al. Microb Pathog. 2014, 75:21-8.
[3] Yu-zhou Guim, et al. Acta Pharmacol Sin. 2016, 37(10): 1337-1348.

Synonyms

Lup-20(29)-ene-3,28-diol, (3β)-

Lup-20(29)-ene-3β,28-diol

Lup-20(30)-ene-3β,28-diol

3aH-Cyclopenta[a]chrysene, lup-20(29)-ene-3,28-diol deriv.

(3β)-Lup-20(29)-ene-3,28-diol

Betuline

Betulin

Betulinol

Trochol

Betulol

3β,28-Dihydroxylup-20(29)-ene

NSC 4644

Betulinic alcohol

(+)-Betulin

3,28-Dihydroxy-lupeol