CAS: 474-62-4; Campesterol

该化合物是一种植物性激素,一种在结构上与胆固醇相似的植物性激素,在各种植物来源中,特别是在植物油,坚果和种子中常见.Campesterol的分子分子配方为C27H46O,具有典型的类固醇结构,其中包括一种四环核心,在C3位置上有一个氢氧基(OH),这种化合物有其潜在的健康利益,特别是在胆固醇管理方面,因为它有助于降低作为平衡饮食的一部分消费的LDL胆固醇水平.Campesterol在植物生理学中的角色也得到承认,它有助于膜结构和功能.从物理特性来看,它通常是白色到白的晶状固体,水溶性低,但有机溶剂溶性较高.它存在于食品中,常常与与心脏健康和胆固醇减少有关的健康索赔有关,因此它成为营养研究和饮食补充的主体.

结构式图片

欧盟法规

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上下游产品

campesteryl acetate 24ξ-flour°Cholesterol 20ξ-fluor°Cholesterol 22ξ-fluor°Cholesterol24-methylcholest-5-en-3β-yl acetate benzoic acid-(ergosten-(5)-yl-(3β)-ester) R)-3c-(4-nitro-benzoyloxy)-10r.13c-dimethyl-17c-((1R:4S)-1.4.5-trimethyl-hexyl)-(8cH.8tH.14tH)-Δ5-tetradecahydro-1H-cyclopenta[a]phenanthrene(10R)-3c-(4-nitro-benzoyloxy)-10r.13c-dimethyl-17c-((1R:4S)-1.4.5-trimethyl-hexyl)-(8cH.8tH.14tH)-Δ5-tetradecahydro-1H-cyclopenta[a]phenanthrene 29H50°C29H50O

合成工艺路线路线简述

    📜(3Beta)-3-[(四氢-2H-吡喃-2-基)氧基]-胆-5-烯-24-醛置于盐酸,正丁基锂,Morus Alba,重水,三苯基膦体系中,用 吡啶 作为反应溶剂,化学反应生成 菜油甾醇
    参考文献:高等植物谷甾醇侧链生物合成中第二次甲基化的机制:桑白细胞培养物中24-亚甲基胆固醇的28个氢的代谢命运
    标题:高等植物谷甾醇侧链生物合成中第二次甲基化的机制:桑白细胞培养物中24-亚甲基胆固醇的28个氢的代谢命运
    摘要:高等植物中谷甾醇侧链的生物合成涉及通过s-腺苷甲硫氨酸的攻击的两个甲基化步骤.研发了第二甲基化的立体化学特征,即在高等植物中从24-亚甲基胆固醇向异黄甾醇的转化.将合成的[28 E-2 H]-和[28 Z-2 H]-24-亚甲基胆固醇喂入桑树桑树的培养细胞中,然后对所得异黄甾醇进行2 H NMR分析,结果表明第二甲基化以这种方式进行甲基的添加和质子损失发生在原始δ24 (28)的相对面上-双键.
    DOI:10.1016/s0040-4039(00)00428-7

    海关参考信息

    专利信息


    专利号:US-11479577-B2
    优先权日:2016-05-18
    标题:Intermediates for the synthesis of bile acid derivatives, in particular of obeticholic acid
    发明人:WEYMOUTH-WILSON ALEXANDER; KOMSTA ZOFIA; WALLIS LAURA; EVANS TIMOTHY; DAVIES IEUAN; OTTER CARL; BATCHELOR RHYS
    权利人:NZP UK LTD
    摘要:The present invention relates to compounds which are intermediates in the synthesis of bile acid derivatives with pharmacological activity. The invention relates to compounds of general formula (I):wherein:, R1, R2, R3, R4, R5, R6 and Y are as defined herein.The compounds are intermediates in the synthesis of synthetic bile acids which are useful in the treatment of conditions such as liver disease. In addition, the invention relates to a method of synthesizing these intermediates and a method of preparing obeticholic acid and obeticholic acid analogues from the compounds of the invention.

    专利号:US-12358871-B2
    优先权日:2019-05-15
    标 题:Photochemical synthesis of vitamin D3 using sensitizers
    发明人:DATLA ANUPAMA; NAGRE PRASHANT; TAMORE JAGDISH; TRIVIKRAM SREENATH; DEGAONKAR GAJANAN
    权利人:FERMENTA BIOTECH LTD
    摘要:The present invention discloses an improved photochemical synthesis of vitamin D3 from 7-dehydrocholesterol alone or in combination with sterol precursors in presence of the photosensitizer of Formula I in high yield and with reduced levels of impurities.

    专利号:US-4360470-A
    优先权日:1980-10-22
    标题 :Process and intermediates for the synthesis of Vitamin D3 metabolites and chenodeoxycholic acid
    发明人:BATCHO ANDREW D; USKOKOVIC MILAN R; WOVKULICH PETER M
    权利人:HOFFMANN LA ROCHE
    摘要:The present disclosure is directed to a process for the synthesis of chenodeoxychloic acid, 25-hydroxycholesterol and 1α,25-dihydroxycholesterol from 17-keto steroids. A cholic acid side chain is stereospecifically introduced by reaction of the appropriate 17-keto steroid with ethyltriphenylphosphonium halides to produce the 17-ethylidene derivative which is allowed to react with acrylic acid esters or propiolic acid esters followed by hydrogenation.

    专利号:US-4310467-A
    优先权日:1980-10-22
    标题:Process and intermediates for the synthesis of vitamin D3 metabolites
    发明人:BATCHO ANDREW D; BERGER JR DONALD E; USKOKOVIC MILAN R
    权利人:HOFFMANN LA ROCHE
    摘要:The present disclosure is directed to a process and intermediates for the synthesis of Vitamin D 3 metabolites such as 1,25-dihydroxycholecalciferol, 25-hydroxycholecalciferol and 24R,25-dihydroxycholecalciferol from 17-keto steroids via intermediates having the natural steroid configuration at the 20-position. These novel intermediates are prepared from 17-keto steroids by reaction with ethyltriphenylphosphonium halides followed by reaction with formaldehyde to form comounds having the natural steroid configuration at the 20-position and which are suitable substrates for the preparation of the aforementioned Vitamin D 3 metabolites.

    专利号:US-11547655-B2
    优先权日:2017-08-02
    标 题:Use of an extract of the pericarp of Nephelium lappaceum for hydrating the skin and/or mucous membranes
    发明人:BONNET ISABELLE; CADAU SÉBASTIEN; DANOUS LOUIS; DERCEVILLE CHARLOTTE; LEOTY-OKOMBI SABRINA
    权利人:BASF BEAUTY CARE SOLUTIONS FRANCE S A S
    摘要:A subject of the present invention is the cosmetic use of a pericarp extract of the plant Nephelium lappaceum for maintaining and/or increasing the hydration and/or the barrier effect of the skin and/or of the mucous membranes. The pericarp extract increases involucrin synthesis and the hyaluronic acid content and the synthesis of ATP and of the taurine transporter TAUT. Another subject of the invention relates to a cosmetic care process comprising the topical application of the pericarp extract of N. lappaceum. Finally, a subject of the invention relates to the pericarp extract for use, in particular dermatological use, thereof in the treatment and/or prevention of pathological conditions caused by a state of abnormal dryness of the skin and/or of the mucous membranes.

    专利号:US-8147883-B1
    优先权日:1999-09-22
    标题:Use of a plant oil product as an agent for increasing the synthesis of skin lipids
    发明人:MSIKA PHILIPPE; PICCIRILLI ANTOINE
    权利人:MSIKA PHILIPPE; PICCIRILLI ANTOINE; EXPANSCIENCE LAB
    摘要:The invention concerns the use of at least a vegetable oil product selected among the group consisting of vegetable oil oleic distillates, vegetable oil unsaponifiable matters, vegetable oil furan lipids and mixtures thereof, as agents for increasing skin lipid synthesis, in particular lipids of the epidermal skin barrier, in or for preparing a composition containing a pharmaceutically or dermatologically acceptable medium. The use enables to prevent and/or treat deterioration of the skin barrier (dry skin, skin subjected to actinic radiation, ichthyosis, acne, xerosis, atopic dermatitis, sensitive skin, chafing and reactive skin, itching and the like).

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    主要参考文献


    1: Mi J, Jiang Q, Qi Z, Liu Z, Bai X, Zheng X, Wu J, Fang Y, Yang A, Chen H. Plasma campesterol and ABCG5/ABCG8 gene loci on the risk of cholelithiasis and cholecystitis: evidence from Mendelian randomization and colocalization analyses. Hum Genomics. 2024 Feb 12;18(1):19. doi: 10.1186/s40246-024-00583-y.
    2: Nunes VS, de Campos EVS, Baracat J, França V, Gomes ÉIL, Coelho RP, Nakandakare ER, Zago VHS, de Faria EC, Quintão ECR. Plasma Campesterol Is Positively Associated with Carotid Plaques in Asymptomatic Subjects. Int J Mol Sci. 2022 Oct 9;23(19):11997. doi: 10.3390/ijms231911997.
    3: Qian YD, Tan SY, Dong GR, Niu YJ, Hu CY, Meng YH. Increased campesterol synthesis by improving lipid content in engineered Yarrowia lipolytica. Appl Microbiol Biotechnol. 2020 Aug;104(16):7165-7175. doi: 10.1007/s00253-020-10743-4. Epub 2020 Jun 26. 20(7):e202300536. doi: 10.1002/cbdv.202300536. Epub 2023 Jul 4. Molecular Docking Studies. Chem Biodivers. 2023 Dec;20(12):e202301534. doi: 10.1002/cbdv.202301534. Epub 2023 Nov 28.

    合成参考文献


    参考文献:10.3390/md9061024
    摘要:Kotake-Nara E, Nagao A. Absorption and metabolism of xanthophylls. Mar Drugs. 2011;9(6):1024–37.
    参考文献:10.1007/s00299-011-1119-6
    摘要:Burlini N, Iriti M, Daghetti A, Faoro F, Ruggiero A, Bernasconi S. Benzothiadiazole (BTH) activates sterol pathway and affects vitamin D3 metabolism in Solanum malacoxylon cell cultures. Plant Cell Rep. 2011 Nov;30(11):2131–41. doi: 10.1007/s00299-011-1119-6.
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