66735
α-亚甲基-γ-丁内酯
purum, ≥97.0% (GC)
别名:
2-甲烯基丁内酯, Tulipane
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关于此项目
经验公式（希尔记法）:
C5H6O2
化学文摘社编号:
分子量:
98.10
PubChem Substance ID:
UNSPSC Code:
12352100
Beilstein/REAXYS Number:
107939
MDL number:
SMILES string
C=C1CCOC1=O
InChI
1S/C5H6O2/c1-4-2-3-7-5(4)6/h1-3H2
InChI key
GSLDEZOOOSBFGP-UHFFFAOYSA-N
grade
purum
assay
≥97.0% (GC)
contains
~1% 2,6-di-tert-butyl-4-methylphenol as stabilizer
bp
86-88 °C/12 mmHg (lit.)
density
1.119 g/mL at 25 °C (lit.)
storage temp.
2-8°C
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Application
强反应性 Michael 受体；α-亚甲基-γ-丁内酯环系存在于许多具有生物学意义的天然产物中
signalword
Warning
hcodes
Hazard Classifications
Aquatic Chronic 3 - Flam. Liq. 3 - Skin Sens. 1
存储类别
3 - Flammable liquids
flash_point_f
98.6 °F - closed cup
flash_point_c
37 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
法规信息
新产品
此项目有
Jean-Pierre Lepoittevin et al.
Chemical record (New York, N.Y.), 9(5), 258-270 (2009-11-26)
Natural products containing an alpha-methylene-gamma-butyrolactone moiety, mainly of the sesquiterpene type, are widely observed in plants, which upon coming into contact with skin, will induce major skin toxicological side effects or phytodermatitis. Indeed two main dermatological pathologies have been associated
Javier A Menendez et al.
Drug news & perspectives, 18(6), 375-385 (2005-10-26)
Fatty acid synthase (FAS)-catalyzed de novo fatty acid biosynthesis, an anabolic energy-storage pathway largely considered of minor importance in humans, actively contributes to the cancer phenotype by virtue of its ability to specifically regulate the expression and activity of Her-2/neu
Taiji Nomura et al.
Plant physiology, 159(2), 565-578 (2012-04-05)
Tuliposides, the glucose esters of 4-hydroxy-2-methylenebutanoate and 3,4-dihydroxy-2-methylenebutanoate, are major secondary metabolites in tulip (Tulipa gesneriana). Their lactonized aglycons, tulipalins, function as defensive chemicals due to their biological activities. We recently found that tuliposide-converting enzyme (TCE) purified from tulip bulbs
Fernando Torres et al.
Cancer letters, 269(1), 139-147 (2008-06-03)
In this study, we investigated the effect of three synthetic alpha-methylene-gamma-butyrolactones (MBL) on viability of 10 human tumor cell lines and found that these lactones were highly cytotoxic against leukemia cells. Studies performed on HL-60 cells indicate that MBL induce
David M Hodgson et al.
Organic letters, 13(10), 2594-2597 (2011-04-15)
Zinc or a chromium(II) source with 3-(bromomethyl)furan-2(5H)-one (3) and an aldehyde gives β-(hydroxymethylaryl/alkyl)-α-methylene-γ-butyrolactones 5 in good yields and high diastereoselectivities. The methodology is demonstrated in concise syntheses of (±)-hydroxymatairesinol (8) and (±)-methylenolactocin (10) by subsequent arylboronate conjugate addition and translactonization
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