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经验公式(希尔记法):
C30H48O3
化学文摘社编号:
分子量:
456.70
UNSPSC Code:
12352002
NACRES:
NA.22
PubChem Substance ID:
EC Number:
201-034-0
Beilstein/REAXYS Number:
2228563
MDL number:
产品名称
熊果酸, ≥90%
InChI key
WCGUUGGRBIKTOS-GPOJBZKASA-N
InChI
1S/C30H48O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1
SMILES string
[H][C@@]12CC[C@]3(C)[C@]([H])(CC=C4[C@]5([H])[C@@H](C)[C@H](C)CC[C@@]5(CC[C@@]34C)C(O)=O)[C@@]1(C)CC[C@H](O)C2(C)C
assay
≥90%
mp
292 °C (dec.) (lit.)
storage temp.
2-8°C
Quality Level
Gene Information
mouse ... Ifng(15978), Nos2(18126)
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Application
熊果酸可作为起始材料,用于与氯乙酸乙酯反应合成熊果酸乙氧甲酰基甲酯(ECU)。ECU可作为关键中间体,用于全合成重要的生物化合物3-乙酰基-2-[(未)取代苯基]-2,3-二氢-1,3,4-噁二唑-5-甲酯 3-O-乙酰基熊果酸。熊果酸也可用于制备新型杂环衍生物,以便进行各种活性研究。
Biochem/physiol Actions
三萜类化合物存在于苹果等各类水果中,它是一种心脏保护剂和抗肿瘤剂。由于它能够抑制淀粉样蛋白β和CD36受体之间的相互作用,因此在研究中被用作潜在的阿尔茨海默氏病治疗剂。
General description
熊果酸(UA)是一种羟基五环三萜酸(HPTA),具有抗菌、 抗癌、 抗氧化和抗炎作用。它还可以促进周围神经损伤后的神经再生。UA可以激活GABA能神经递质系统,从而延长睡眠持续时间。[GABA= γ-氨基丁酸]
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
580.5 °F
flash_point_c
304.7 °C
ppe
Eyeshields, Gloves, type N95 (US)
Synthesis of novel ursolic acid heterocyclic derivatives with improved abilities of antiproliferation and induction of p53, p21waf1 and NOXA in pancreatic cancer cells
Leal AS, et al.
Bioorganic & Medicinal Chemistry, 20(19), 5774-5786 (2012)
Synthesis and anti-inflammatory activity of 3-acetyl-2-[(un) substituted phenyl]-2, 3-dihydro-1, 3, 4-oxadiazol-5-methyl 3-O-acetylursolate
Ding-Ju Y, et al.
Chinese Journal of Organic Chemistry, 28(6), 1055-1060 (2008)
Ursolic acid protects hippocampal neurons against kainate-induced excitotoxicity in rats.
Shih YH, et al.
Neuroscience Letters, 363(2), 136-140 (2004)
Aljawharah AlQathama et al.
Biomolecules, 10(6) (2020-06-18)
We evaluate how 3-acetylation modulates the in vitro activity of ursolic acid in melanoma cells alone or in combination treatments with quercetin. Anti-proliferative studies on A375 cells and adult human dermal fibroblasts included analyses on cell cycle distribution, caspase activity
Ursolic acid induces neural regeneration after sciatic nerve injury.
Liu B, et al.
Neural Regeneration Research, 8(27), 2510-2510 (2013)
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