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B8936

Sigma-Aldrich

Betulinsäure

≥98% (HPLC)

Synonym(e):

3β-Hydroxy-20(29)-lupaene-28-oic acid, Mairin

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About This Item

Empirische Formel (Hill-System):
C30H48O3
CAS-Nummer:
472-15-1
Molekulargewicht:
456.70
EG-Nummer:
207-448-8
MDL-Nummer:
MFCD00009619
UNSPSC-Code:
12352205
PubChem Substanz-ID:
329773146
NACRES:
NA.25
Preise und Verfügbarkeit sind derzeit nicht verfügbar.

Assay

≥98% (HPLC)

Form

powder

mp (Schmelzpunkt)

295-298 °C (dec.) (lit.)

Anwendung(en)

metabolomics
vitamins, nutraceuticals, and natural products

Lagertemp.

2-8°C

SMILES String

CC(=C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)C(O)=O

InChI

1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1

InChIKey

QGJZLNKBHJESQX-FZFNOLFKSA-N

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Verwandte Kategorien

Allgemeine Beschreibung

Betulinic acid (BetA) is a natural product mostly sourced from the birch tree (Betula spp.).[1] This pentacyclic lupanetype triterpenoid is also associated with other species such as Syzygium spp., Diospyros spp., Ziziphus spp., and Paeonia spp..[1]

Anwendung

Betulinic acid (BetA) has been used:
  • to test its effects as an antiviral agent against Dengue virus (DENV)[2]
  • as a sterol regulatory element-binding protein (SREBP) inhibitor to repress the lipid metabolism and proliferation of clear cell renal cell carcinoma (ccRCC) cells[3]
  • as a treatment to test its anti-tumor properties for cell viability and apoptotic cell death assays in multiple myeloma models[4]

Biochem./physiol. Wirkung

Betulinic acid displays many biological and pharmacological properties such as anticancer, anti-inflammatory, anti-bacterial, anti-human immunodeficiency virus (HIV), and anti-malarial properties.[1]
Betulinic acid, a pentacyclic triterpene, selectively induces apoptosis in tumor cells by directly activating the mitochondrial pathway of apoptosis through a p53- and CD95-independent mechanism.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
0000324362
0000324362
0000251243
0000251244
0000251244

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SREBP-Verarbeitungsinhibitor, Betulin, CAS-Nr. 473-98-3, Calbiochem The SREBP Processing Inhibitor, Betulin, also referenced under CAS 473-98-3, controls the biological activity of SCAP (SREBP cleavage activating protein). This small molecule/inhibitor is primarily used for Cell Signaling applications.

Sigma-Aldrich

569371

SREBP-Verarbeitungsinhibitor, Betulin, CAS-Nr. 473-98-3, Calbiochem

Hirsutenone ≥95% (LC/MS-ELSD)

Sigma-Aldrich

SMB00096

Hirsutenone

Betulonsäure phyproof® Reference Substance

PHL83839

Betulonsäure

Lupeol analytical standard

Supelco

18692

Lupeol

Oregonin ≥95% (LC/MS-ELSD)

Sigma-Aldrich

SMB00088

Oregonin

Betulin phyproof® Reference Substance

PHL89581

Betulin

Sasithon Senamontree et al.
PeerJ, 9, e12321-e12321 (2021-11-02)
Controlling cellular functions, including stem cell growth and differentiation, can be the key for the treatment of metabolic disorders, such as type II diabetes mellitus (T2DM). Previously identified as peroxisome proliferator-activated receptor gamma (PPARγ) antagonist, betulinic acid (BA) may have
Franziska B Mullauer et al.
Anti-cancer drugs, 22(3), 223-233 (2011-01-26)
Betulinic acid (BetA) is a plant-derived pentacyclic triterpenoid with potent anticancer capacity that targets the mitochondrial pathway of apoptosis. BetA has a broad efficacy in vitro against prevalent cancer types, including lung, colorectal, prostate, cervix and breast cancer, melanomas, neuroblastomas
Biological activity of betulinic acid: a review
Moghaddam M G, et al.,
Pharmacology & Pharmacy (2012)
Rita C Santos et al.
Bioorganic & medicinal chemistry, 17(17), 6241-6250 (2009-08-14)
A series of new imidazole carboxylic esters (carbamates) and N-acylimidazole derivatives of betulin and betulinic acid (14-29) have been synthesized. The new compounds were screened for in vitro cytotoxicity activity against human cancer cell lines HepG2, Jurkat and HeLa. A
Sami Alakurtti et al.
Bioorganic & medicinal chemistry, 18(4), 1573-1582 (2010-02-02)
Betulin, a naturally occurring abundant triterpene is converted in four steps to 3,28-di-O-acetyllupa-12,18-diene. When various 4-substituted urazoles were oxidized to the corresponding urazines with iodobenzene diacetate in the presence of 3,28-di-O-acetyllupa-12,18-diene, new heterocyclic betulin derivatives were produced. These betulin derivatives
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Fragen

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 Antwort

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 Antwort

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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