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Merck

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:
Molekulargewicht:
456.70
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352205
PubChem Substanz-ID:
NACRES:
NA.25
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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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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


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Kunden haben sich ebenfalls angesehen

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)
Jimin Shin et al.
PloS one, 6(6), e21492-e21492 (2011-07-07)
Signal transducer and activator of transcription 3 (STAT3) is a transcription factor that regulates various cellular processes such as cell survival, angiogenesis and proliferation. In the present study, we examined that betulinic acid (BA), a triterpene from the bark of
Marcus Wing Choy Loe et al.
Antiviral research, 184, 104954-104954 (2020-10-21)
Dengue virus (DENV) is an arthropod-borne virus that has developed into a prominent global health threat in recent decades. The main causative agent of dengue fever, the virus infects an estimated 390 million individuals across the globe each year. Despite

Questions

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

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    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 answer
    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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