与本品存在于牛、羊和猪的胆汁中。为无色片状物或白色结晶粉末。味道是先甜后苦。无水物熔点为198℃,比旋光度为+37。(乙醇中)。pK。 6.4。可溶于碱金属氢氧化物或碳酸盐的溶液中。
有乙醇结晶法和乙酸乙酯分离法。乙酸乙酯分离法是利用乙酸乙酯溶解除去脱氧胆酸,然后再用乙醇进一步纯化而得产品。牛、羊胆汁中加入1/10量的氢氧化钠,加热至沸,水解18h。水解液冷却,倾出上清液,下层过滤。上清液与滤液合并,加30%硫酸使pH为2~3,此时粗胆酸浮在液层。取上浮物,加等量水煮沸10~20min,使成颗粒状沉淀,再反复用水漂洗至中性,50~60℃干燥,得粗胆汁酸。取粗胆汁酸,捣碎,加0. 75倍75%乙醇,加热搅拌,回流至固体物充分溶解,然后在O~5℃使其结晶。结晶抽滤或离心甩干,用少量80%乙醇洗涤,干燥,得胆酸粗结晶。取胆酸粗结晶加4倍量95%乙醇和4%~5%活性炭,加热,搅拌,回流,待充分溶解后,趁热过滤。滤液浓缩至约1/4体积,置O~5℃结晶。
本品可作为乳化剂使用。
中文名 | 胆酸 |
英文名 | Cholic acid |
别名 | 胆酸 胆酸 来源牛和羊 熊去氧胆酸EP杂质B 3α,7α,12α-三羟基-5β-胆烷酸 |
英文别名 | Cholic acid 3,7,12-TRIHYDROXYCHOLANIC ACID 3,7,12-Trihydroxy-cholan-24-oic acid 3A,7A,12A-TRIHYDROXY-5B-CHOLAN-24-OIC ACID 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acid 3ALPHA, 7ALPHA, 12ALPHA-TRIHYDROXY-5BETA-CHOLANIC ACID 3ALPHA,7ALPHA,12ALPHA-TRIHYDROXY-5BETA-CHOLAN-24-IC ACID 3ALPHA,7ALPHA,12ALPHA-TRIHYDROXY-5BETA-CHOLAN-24-OIC ACID 5beta-Cholan-24-oic acid, 3alpha,7alpha,12alpha-trihydroxy- (3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxycholan-24-oic acid Cholan-24-oic acid, 3,7,12-trihydroxy-, (3alpha,5beta,7alpha,12alpha)- (3alpha,5beta,7alpha,8xi,12alpha,20xi)-3,7,12-trihydroxycholan-24-oic acid (4R)-4-[(3S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid |
CAS | 81-25-4 |
EINECS | 201-337-8 |
化学式 | C24H40O5 |
分子量 | 408.58 |
InChI | InChI=1/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14?,15+,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1 |
InChIKey | BHQCQFFYRZLCQQ-OELDTZBJSA-N |
密度 | 1.0310 (rough estimate) |
熔点 | 200-201 °C (lit.) |
沸点 | 449.08°C (rough estimate) |
比旋光度 | 36 º (c=0.6, 95% EtOH) |
闪点 | 9℃ |
水溶性 | 0.28 g/L (15 ºC) |
蒸汽压 | 4.59E-16mmHg at 25°C |
溶解度 | 甲醇: 0.1g/ml,澄清 |
折射率 | 1.5800 (estimate) |
酸度系数 | 4.98(at 20℃) |
存储条件 | 2-8°C |
敏感性 | Easily absorbing moisture |
外观 | 整洁 |
颜色 | White to Brown |
Merck | 14,2203 |
BRN | 2822009 |
物化性质 | 本品存在于牛、羊、猪的胆汁中。为无色片状物或白色结晶粉末。有些苦味,尝后又有些甜的感觉。Mp198℃,比旋度(c=0.6,乙醇)为+37°。1g胆酸约溶于300ml乙醇或丙酮,7ml冰醋酸,很少量溶于水。一水合物为白色片状结晶。1927年,H.Wieland(德国)研究胆酸组成,获诺贝尔化学奖。 |
MDL号 | MFCD00003672 |
危险品标志 | Xi - 刺激性物品![]() |
风险术语 | 36/37/38 - 刺激眼睛、呼吸系统和皮肤。 |
安全术语 | S24/25 - 避免与皮肤和眼睛接触。 S36 - 穿戴适当的防护服。 S26 - 不慎与眼睛接触后,请立即用大量清水冲洗并征求医生意见。 |
危险品运输编号 | UN1230 - class 3 - PG 2 - Methanol, solution |
WGK Germany | 2 |
RTECS | FZ9350000 |
TSCA | Yes |
海关编号 | 29181990 |
上游原料 | 硫酸 乙醇 |
下游产品 | 甘氨胆酸 3Α,7Α-二羟基-12-羰基-5Β-胆烷酸 去氢胆酸 去水膽酸 |
参考资料 展开查看 | 1. 曹妍, 宋青青, 李军,等. 牦牛胆中胆汁酸类化学成分分析[J]. 中国中药杂志 2019年44卷12期, 2538-2543页, MEDLINE ISTIC PKU CSCD CA BP, 2019. 2. 李玮,蒋珍珍,李菡,屠鹏飞,宋青青,于娟,宋月林.利用在线加压溶剂提取-超高效液相色谱-离子阱-飞行时间-质谱法定性分析片仔癀化学成分组[J].色谱,2021,39(05):478-487. 3. 王健,孙瑜,陈莉莉,韩真真,孙精通.基于~1H-NMR代谢组学技术评价何首乌炮制品中差异代谢物的研究[J].现代药物与临床,2020,35(08):1537-1543. 4. Ling, Ziting, et al. "Fabrication egg white gel hydrolysates-stabilized oil-in-water emulsion and characterization of its stability and digestibility." Food Hydrocolloids 102 (2020): 105621.https://doi.org/10.1016/j.foodhyd.2019.105621 5. Wu, Wanqin, et al. "Improvement of the probiotic potential and yield of Lactobacillus rhamnosus cells using corn steep liquor." LWT 131 (2020): 109862.https://doi.org/10.1016/j.lwt.2020.109862 6. Lu, Xiaoguang, et al. "Calycosin attenuates doxorubicin-induced cardiotoxicity via autophagy regulation in zebrafish models." Biomedicine & Pharmacotherapy 137 (2021): 111375.https://doi.org/10.1016/j.biopha.2021.111375 7. Song Lin, Tian-yang Wang, Hua-rong Xu, Xin-nong Zhang, Qi Wang, Ran Liu, Qing Li, Kai-shun Bi,A systemic combined nontargeted and targeted LC-MS based metabolomic strategy of plasma and liver on pathology exploration of alpha-naphthylisothiocyanate induce 8. [IF=3.935] Ziying Liu et al."Promotion of classic neutral bile acids synthesis pathway is responsible for cholesterol-lowing effect of Si-miao-yong-an decoction: Application of LC–MS/MS method to determine 6 major bile acids in rat liver and plasma."J Pharmaceut Bio 9. [IF=9.147] Ziting Ling et al."Fabrication egg white gel hydrolysates-stabilized oil-in-water emulsion and characterization of its stability and digestibility."Food Hydrocolloid. 2020 May;102:105621 10. [IF=5.396] Shiming Huang et al."A sulfated polysaccharide from Gracilaria Lemaneiformis regulates cholesterol and bile acid metabolism in high-fat diet mice."Food Funct. 2019 Jun;10(6):3224-3236 11. [IF=5.34] Kaihui Zhang et al."A UPLC-MS/MS-based metabolomics analysis of the pharmacological mechanisms of rabdosia serra against cholestasis."Phytomedicine. 2021 Oct;91:153683 12. [IF=4.952] Wanqin Wu et al."Improvement of the probiotic potential and yield of Lactobacillus rhamnosus cells using corn steep liquor."Lwt Food Sci Technol. 2020 Sep;131:109862 13. [IF=3.935] Song Lin et al."A systemic combined nontargeted and targeted LC-MS based metabolomic strategy of plasma and liver on pathology exploration of alpha-naphthylisothiocyanate induced cholestatic liver injury in mice."J Pharmaceut Biomed. 2019 Jul;171:180 14. [IF=3.935] Runjing Zhang et al."Xiaoyan lidan formula ameliorates α-naphthylisothiocyanate-induced intrahepatic cholestatic liver injury in rats as revealed by non-targeted and targeted metabolomics."J Pharmaceut Biomed. 2020 Feb;179:112966 15. [IF=1.618] Chen Mengjun et al."A Powerful HPLC-ELSD Method for Simultaneous Determination of Fecal Bile Acids in T2DM Rats Interfered by Sanhuang Xiexin Tang."J Chromatogr Sci. 2021 Sep;59(9):871-876 16. [IF=5.396] Juan Wu et al."Sargassum fusiforme polysaccharide is a potential auxiliary substance for metformin in the management of diabetes."Food Funct. 2022 Feb;: 17. [IF=6.558] Yan Cao et al."Widely quasi-quantitative analysis enables temporal bile acids-targeted metabolomics in rat after oral administration of ursodeoxycholic acid."ANALYTICA CHIMICA ACTA. 2022 Jun;1212:339885 |
与本品存在于牛、羊和猪的胆汁中。为无色片状物或白色结晶粉末。味道是先甜后苦。无水物熔点为198℃,比旋光度为+37。(乙醇中)。pK。 6.4。可溶于碱金属氢氧化物或碳酸盐的溶液中。
有乙醇结晶法和乙酸乙酯分离法。乙酸乙酯分离法是利用乙酸乙酯溶解除去脱氧胆酸,然后再用乙醇进一步纯化而得产品。牛、羊胆汁中加入1/10量的氢氧化钠,加热至沸,水解18h。水解液冷却,倾出上清液,下层过滤。上清液与滤液合并,加30%硫酸使pH为2~3,此时粗胆酸浮在液层。取上浮物,加等量水煮沸10~20min,使成颗粒状沉淀,再反复用水漂洗至中性,50~60℃干燥,得粗胆汁酸。取粗胆汁酸,捣碎,加0. 75倍75%乙醇,加热搅拌,回流至固体物充分溶解,然后在O~5℃使其结晶。结晶抽滤或离心甩干,用少量80%乙醇洗涤,干燥,得胆酸粗结晶。取胆酸粗结晶加4倍量95%乙醇和4%~5%活性炭,加热,搅拌,回流,待充分溶解后,趁热过滤。滤液浓缩至约1/4体积,置O~5℃结晶。
本品可作为乳化剂使用。
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