Betulinic Acid 桦木酸

CAS 472-15-1 MFCD00009619

化学结构图

472-15-1
SMILES: C=C(C)[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12

化学属性

Mol. FormulaC30 H48 O3
Mol. Weight456.7
Melting Point295-298
Density1.065
Refractive index7.8 ° (C=0.9, Pyridine)
Appearance Solid powder
SolubilitySoluble in DMSO, not in water

别名和识别编码

Chemical NameBetulinic Acid
CAS Number472-15-1
Synonym (3?)-3-HydroxyLup-20(29)-en-28-oic Acid 01653 l 3-B-HYDROXY-LUPA-20(30)-ENE 28-OIC ACID 3-epi-betulinic acid 3?-Hydroxylup-20(29)-en-28-oic Acid 3B-HYDROXY-20(29)-LUPENE-28-OIC ACID 3BETA-HYDROXY-20(29)-LUPAENE-28-OIC ACID 3BETA-HYDROXY-20(29)-LUPENE-28-OIC ACID 3β-Hydroxy-20(29)-lupaene-28-oic Acid 3β-hydroxy-20(29)-lupaene-28-oic acid 545-47-1 ?-Betulinic Acid ALS357; ALS 357; ALS-357; Mairin. BETULICACID: LUP-20(29)-EN-28-OICACID, 3-HYDROXY-, (3B)-, BETULINIC ACID BETULINIC ACID WITH HPLC BETULINIC ACID hplc BETULINIC ACID, TECH., 90% Betulinic Acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {
MDL NumberMFCD00009619
EC Number207-448-8
Reaxys-RN2824245
PubChem Substance ID64971
Merck Number1190
Beilstein Registry Number2824245
Chemical Name Translation桦木酸
LabNetwork Molecule IDLN00188803
InChIInChI=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
FormulaC30H48O3
IUPAC Name(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid
InChIKeyQGJZLNKBHJESQX-FZFNOLFKSA-N
Canonical SMILESO=C([C@]1(CC[C@H]2C(C)=C)[C@@]2([H])[C@@]3([H])CC[C@]4([H])[C@@]5(C)CC[C@H](O)C(C)(C)[C@]5([H])CC[C@@]4(C)[C@]3(C)CC1)O
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分类

  • {SNA} Biochemicals and R
  • {SNA} Anti-proliferative Agents, Asymmetric Synthesis, Chemical Synthesis, Chiral Building Blocks, Complex Molecules, 化学预防剂, 癌症研究,
  • {SNA} Biochemicals and Reagents, Cell Biology, Isoprenoids,
  • {SNA} Anti-proliferative Agents, Asymmetric Synthesis, Chemical Synthesis, Chemopreventive Agents, Chiral Building Blocks, Complex Molecules, 癌症研究, 细胞生物学
  • {SNA} Isoprenoids, Phytochemicals by Chemical Classification, Prenols, Saponins, 生化试剂, 细胞生物学, 脂类, 营养研究
  • {SNA} Anti-proliferative Ag

产品应用

  • Betulinic acid is a pentacyclic lupane-type triterpene derivative of betulin (isolated from the bark of Betula alba, the common white birch) with antiinflammatory, anti-HIV and antineoplastic activities. Betulinic acid induces apoptosis through induction of changes in mitochondrial membrane potential, production of reactive oxygen species, and opening of mitochondrial permeability transition pores, resulting in the release of mitochondrial apogenic factors, activation of caspases, and DNA fragmentation. Although originally thought to exhibit specific cytotoxicity against melanoma cells, this agent has been found to be cytotoxic against non-melanoma tumor cell types including neuroectodermal.and brain tumor cells.

相关文献及参考

  • [2]. Gao Y, et al. Betulinic acid induces apoptosis and ultrastructural changes in MDA-MB-231 breast cancer cells. Ultrastruct Pathol. 2018 Jan-Feb;42(1):49-54.
  • [3]. Kalra J, et al. Betulinic acid alleviates dextran sulfate sodium-induced colitis and visceral pain in mice. Naunyn Schmiedebergs Arch Pharmacol. 2017 Dec 26.
  • [4]. Hashimoto F, et al. Anti-AIDS agents--XXVII. Synthesis and anti-HIV activity of betulinic acid and dihydrobetulinic acid derivatives. Bioorg Med Chem. 1997 Dec;5(12):2133-43.
  • [5]. Kasperczyk H, et al. Betulinic acid as new activator of NF-kappaB: molecular mechanisms and implications for cancer therapy. Oncogene. 2005 Oct 20;24(46):6945-56.
  • Merck: 14,1190
  • Merck: 14,1190 Beilstein: 10,III,1059
  • Pisha, E. et al.: Nat. Med., 1, 1046 (1995); Fulda, S. et al.: Cancer Res., 57, 4956 (1997); Kashiwada, Y. et al.: J. Med. Chem., 39, 1016 (1996); Genet, C. et al.: J. Med. Chem., 53, 178 (2010);
  • [1]. Chowd

安全信息

WGK Germany3
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
Signal word Warning
GHS Symbol
Safety Statements
Risk Statements
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
Precautionary statements
Storage condition +4°C Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). 储存温度 2-8°C
Hazard Codes Xi

其他信息

  • Sigma Aldrich:472-15-1(sigmaaldrich)
  • 白桦脂酸价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 B2836 白桦脂酸 Betulinic Acid 100MG 895元
  • 图谱信息:白桦脂酸(472-15-1)红外图谱(IR1)
  • MOL 文件:472-15-1.mol
  • TCI Shanghai:白桦脂酸 Betulinic Acid,>;97.0%(GC)(T)(472-15-1)

系列性分类

  1. Life Science 生命科学
  2. Cancer Research
  3. Chemopreventive Agents - Cancer Research
  4. Anti-proliferative Agents - Chemopreventive Agents
  1. Life Science 生命科学
  2. Nutrition Research 营养研究
  3. Phytochemicals by Chemical Classification - Nutrition Research
  4. Saponins - Phytochemicals by Chemical Classification
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Lipids - Biochemicals and Reagents
  4. Prenols - Lipids
  5. Isoprenoids - Prenols
  1. Chemical Synthesis 化学合成
  2. Asymmetric Synthesis 不对称合成
  3. Chiral Building Blocks 手性分子砌块
  4. Complex Molecules - Chiral Building Blocks
  1. Analytical & Chromatography 分析化学与色谱
  2. Analytical Standards
  3. Chromatography - Analytical Standards
  4. Life Sciences Standards - Chromatography
  5. Phytopharma Standards - Life Sciences Standards
  6. Standards by Plant Genus - Phytopharma Standards
  7. Syzygium - Standards by Plant Genus
  1. Medical Research Areas
  2. DNA Damage
  3. Topoisomerase
  1. Medical Research Areas
  2. Microbiology
  3. HIV Protease
  1. Medical Research Areas
  2. Metabolism
  3. Endogenous Metabolite  (内源性代谢物)

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