94105-90-5
94105-90-5 結(jié)構(gòu)式
基本信息
(+)-雌馬酚
R,S-雌馬酚
納米脂質(zhì)體雌馬酚
(鹵)-EQUOL
雌馬酚,(±)-雌馬酚
雌馬酚 98% 不是S型,混旋的
3-(4-羥基苯基)四氫苯并吡喃-7-醇
(+/-)Equol
(+/-)-EQUOL
Equol,99%e.e.
EQUOL(RACEMIC)
(+/-)-Equol>
(+/-)-Equol (GMP)
7,4'-HoMoisoflavane
(±)-EQUOL >= 99.0% (TLC)
4′,7-Dihydroxyisoflavane
物理化學(xué)性質(zhì)
安全數(shù)據(jù)
制備方法
10499-17-9
531-95-3
在氮?dú)獗Ｗo(hù)下，將化合物3a（0.20 g，0.78 mmol）、n-Bu4NI（1.01 g，2.73 mmol）和無(wú)水CH2Cl2（5 mL）的混合物攪拌并冷卻至-78℃。隨后，向冷卻的混合物中逐滴加入BCl3（1 M，2.73 mL，2.73 mmol）的CH2Cl2溶液。將反應(yīng)混合物攪拌并在2小時(shí)內(nèi)緩慢升溫至0℃。反應(yīng)完成后，用冰水（10 mL）小心淬滅，繼續(xù)攪拌20分鐘，然后用飽和NaHCO3溶液（10 mL）中和。真空濃縮后，用EtOAc（10 mL×0.5）萃取殘余物。合并有機(jī)層，用無(wú)水MgSO4干燥。過(guò)濾后，濾液經(jīng)真空濃縮，通過(guò)硅膠柱色譜（乙酸乙酯/正己烷=1:3）純化，得到無(wú)色晶體雌馬酚3b（0.18 g，收率95%）。雌馬酚的性質(zhì)如下：熔點(diǎn)162-164℃（文獻(xiàn)值158℃）；薄層色譜Rf值0.24（乙酸乙酯/正己烷=1:3）；紅外光譜（KBr）νmax：3231, 2897, 1598, 1510, 1470, 1366, 1252, 1158, 1119, 826 cm-1；1H-NMR（400 MHz, DMSO-d6）δ：2.80（m, 2H, H-3和H-4a），3.01（m, 1H, H-4b），3.89（t, J=10.4 Hz, 1H, H-2a），4.14（d, J=10.4 Hz, 1H, H-2b），6.20（d, J=2.4 Hz, 1H, H-8），6.29（dd, J=8.4, 2.4 Hz, 1H, H-6），6.72（d, J=8.4 Hz, 2H, H-3', H-5'），6.86（d, J=8.4 Hz, 1H, H-5），7.10（d, J=8.4 Hz, 2H, H-2', H-6'），9.18（s, 1H, OH），9.29（s, 1H, OH）；13C-NMR（100 MHz, DMSO-d6）δ：31.3, 37.2, 70.3, 102.5, 108.0, 112.6, 115.3, 128.3, 130.1, 131.7, 154.5, 156.2, 156.5；電子轟擊質(zhì)譜（70 eV）m/z（相對(duì)強(qiáng)度，百分比）：242（M+, 58），135（25），134（40），123（88），120（100），107（39），91（37）。元素分析計(jì)算值（C15H14O3）：C 74.36，H 5.82；實(shí)測(cè)值：C 74.13，H 5.90。
參考文獻(xiàn)：
[1] Tetrahedron Letters, 2009, vol. 50, # 18, p. 2121 - 2123
[2] Patent: US2010/298581, 2010, A1. Location in patent: Page/Page column 7-8
[3] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 6, p. 1559 - 1567
常見(jiàn)問(wèn)題列表
Equol is first isolated and identified from pregnant-mares' urine and later found in the urine of the goat, cow, hen and sheep. Equol, unlike the soy isoflavones daidzein or genistein, has a chiral center and therefore can occur as 2 distinct diastereoisomers. S-equol is the exclusive product of human intestinal bacterial synthesis from soy isoflavones and both enantiomers are bioavailable. S-equol has a high affinity for estrogen receptor beta (K i =0.73 nM), whereas R-equol is relatively inactive. Equol could promote the proliferation and differentiation of rat osteoblasts through activating the ER-PKCα-related signaling pathway. The alkaline phosphatase activity also increases significantly in all of the equol and 17β-estradiol (E2 ) groups. Equol also significantly elevates the osteocalcin levels.
Equol is a modest natriuretic and vasorelaxant agent in the rat. Orally administered equol is about 8-fold less potent than orally administered furosemide. In isolated aortic rings precontracted by administration of phenylephrine, administration of equol relaxes the contracted aorta (concentration for half-maximal activity 58.9±16 μM). Equol possesses anticancer activity that suppresses tumor formation via apoptosis induction in rats with DMBA-induced mammary gland tumors. In addition, equol shows a hepatic protective effect by acting as an antioxidant and by reducing apoptosis.