Betulin

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Betulin

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Cat No: 11041

Biochemicals - Natural Products

Sterol regulatory element binding protein 2 (SREBP-2) regulates cholesterol synthesis by activating the transcription of genes for HMG-CoA reductase and other enzymes of the cholesterol synthetic pathway.{13851,13853} When cellular sterol levels are hi...

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Territorial Availability: Available through Bertin Technologies only in France

Synonyms:

lup-20(29)-ene-3?,28-diol

Correlated keywords:

1406-58-2 1192133-66-6 betuline betulinic alcohol betulinol betulol NSC4644 NSC-4644 SREBP-2 cholesterol nuclear transcription factors natural products metabolic diseases anti-cancers atherosclerosis triterpene betulinic acids pentacyclic birch trees inhibits inhibitors inhibitions SREBPs SREBP2 SCAP-Insig binding binds ER lipids western-type atherosclerotic plaques LDLR Jurkat A549 carcinoma cells HeLa

Product Overview:
Sterol regulatory element binding protein 2 (SREBP-2) regulates cholesterol synthesis by activating the transcription of genes for HMG-CoA reductase and other enzymes of the cholesterol synthetic pathway.{13851,13853} When cellular sterol levels are high, SREBP is bound by SCAP and Insig to ER membranes as a glycosylated precursor protein. Upon cholesterol depletion, the protein is cleaved to its active form and translocated into the nucleus to stimulate transcription of genes involved in the uptake and synthesis of cholesterol.{13148} Betulin, the precursor of betulinic acid, is a pentacyclic triterpene found in the bark of birch trees. Betulin inhibits the SREBP-driven pathway of cholesterol and fatty acid biosynthesis by promoting SCAP–Insig binding which prevents the activation and release of SREBP-2 from the ER.{19894} At 15-30 mg/kg/day, betulin has been shown to decrease lipid levels and increase insulin sensitivity in mice fed a western-type diet.{19894} In an atherosclerosis disease model, 30 mg/kg/day betulin can reduce the size and improve the stability of atherosclerotic plaques in LDLR-knockout mice.{19894} At 2.5-5 μg/ml betulin, in combination with cholesterol, demonstrates anticancer effects by inducing apoptosis in Jurkat cells, A549 lung carcinoma cells, and HeLa cervical carcinoma cells.{22046}

Size	250 mg
Shipping	dry ice
CAS Number	473-98-3
Molecular Formula	C₃₀H₅₀O₂
SMILES	O[C@H]1CC[C@@]2(C)[C@](CC[C@]3(C)[C@]2([H])CC[C@@]4([H])[C@]3(CC[C@]5(CO)[C@]4([H])[C@H](C(C)=C)CC5)C)([H])C1(C)C
Molecular Weight	442,7
Formulation	A crystalline solid
Purity	≥98%
Custom Code	2907.19
UNSPSC code	12352100

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Cayman Chemical's mission is to help make research possible by supplying scientists worldwide with the basic research tools necessary for advancing human and animal health. Our utmost commitment to healthcare researchers is to offer the highest quality products with an affordable pricing policy.

Our scientists are experts in the synthesis, purification, and characterization of biochemicals ranging from small drug-like heterocycles to complex biolipids, fatty acids, and many others. We are also highly skilled in all aspects of assay and antibody development, protein expression, crystallization, and structure determination.

Over the past thirty years, Cayman developed a deep knowledge base in lipid biochemistry, including research involving the arachidonic acid cascade, inositol phosphates, and cannabinoids. This knowledge enabled the production of reagents of exceptional quality for cancer, oxidative injury, epigenetics, neuroscience, inflammation, metabolism, and many additional lines of research.

Our organic and analytical chemists specialize in the rapid development of manufacturing processes and analytical methods to carry out clinical and commercial GMP-API production. Pre-clinical drug discovery efforts are currently underway in the areas of bone restoration and repair, muscular dystrophy, oncology, and inflammation. A separate group of Ph.D.-level scientists are dedicated to offering Hit-to-Lead Discovery and Profiling Services for epigenetic targets. Our knowledgeable chemists can be contracted to perform complete sample analysis for analytes measured by the majority of our assays. We also offer a wide range of analytical services using LC-MS/MS, HPLC, GC, and many other techniques.

Accreditations
ISO/IEC 17025:2005
ISO Guide 34:2009

Cayman is a leader in the field of emerging drugs of abuse, providing high-purity Schedule I-V Controlled Substances to federally-licensed laboratories and qualified academic research institutions for forensic analyses. We are certified by ACLASS Accreditation Services with dual accreditation to ISO/IEC 17025:2005 and ISO Guide 34:2009.