38030-57-8

• 常用中文名：4-氧代-维A酸
• 常用英文名：all-trans-4-Oxoretinoic acid
• CAS号：38030-57-8
• 分子式：C₂₀H₂₆O₃
• 分子量：314.41900
• 相关类别： 天然产物 其他
• 发布时间：2018-02-10 08:00:00
• 更新时间：2024-01-02 18:07:07
• all-trans-4-Oxoretinoic acid,是维生素A 的活性代谢物,可通过作用核维甲酸受体 (RARs) 来诱导基因转录。

名称

• 中文名: 4-氧代-维A酸
• 英文名: all-trans-4-oxoretinoic acid
• 中文别名: 4-氧代-全反式维甲酸; 3,7-二甲基-9-(4-氧代-2,6,6-三甲基环己烯)-2,4,6,8-全反式壬四烯酸; 4-氧代-视黄酸; 维A酸-4-酮
• 英文别名: 4-keto-Retinoic Acid; 4-oxo-all-rans-retinoic acid; 4-Oxoretinoic Acid; all-trans-4-Oxoretinoic Acid; 4-oxo-all-trans-retinoic acid; all-trans 4-Keto Retinoic Acid; 4-oxo-Retinoic acid; 4-Ketoretinoic Acid; 4-Oxo-atRA; 4-Oxotretinoin

物化性质

• 密度: 1.07g/cm3
• 沸点: 509.9ºC at 760 mmHg
• 熔点: 175-178°C (分解)
• 分子式: C₂₀H₂₆O₃
• 分子量: 314.41900
• 闪点: 276.3ºC
• 精确质量: 314.18800
• PSA: 54.37000
• LogP: 4.78160
• 折射率: 1.565
• 储存条件: 2-8℃

生物活性

• 描述: all-trans-4-Oxoretinoic acid,是维生素A 的活性代谢物,可通过作用核维甲酸受体 (RARs) 来诱导基因转录。
• 相关类别:
  天然产物 >> 其他
  研究领域 >> 代谢疾病
• 靶点:

  Human Endogenous Metabolite

• 体外研究: 全反式-4-氧代氨基酸,维生素A的活性代谢产物,通过与核视黄酸受体(RARs)的结合诱导基因转录[1]。全反式-4-氧代氨基酸是视黄酸(RA)的生物活性几何异构体[2]。
• 参考文献:

  [1]. Topletz AR, et al. Induction of CYP26A1 by metabolites of retinoic acid: evidence that CYP26A1 is an important enzyme in the elimination of active retinoids. Mol Pharmacol. 2015;87(3):430-41.

  [2]. Stahl W, et al. 4-oxo-retinoic acid is generated from its precursor canthaxanthin and enhances gap junctional communication in 10T1/2 cells. Adv Exp Med Biol. 1996;387:121-8.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : VH6599800 CHEMICAL NAME : Retinoic acid, 4-oxo- CAS REGISTRY NUMBER : 38030-57-8 LAST UPDATED : 199007 DATA ITEMS CITED : 5 MOLECULAR FORMULA : C20-H26-O3 MOLECULAR WEIGHT : 314.46 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 100 mg/kg SEX/DURATION : female 11 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - musculoskeletal system REFERENCE : TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 35,33A,1987 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 10 mg/kg SEX/DURATION : female 11 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - musculoskeletal system REFERENCE : TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 100,162,1989 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 20 mg/kg SEX/DURATION : female 8 day(s) after conception TOXIC EFFECTS : Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) REFERENCE : TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 95,122,1988 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 39 mg/kg SEX/DURATION : female 8 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) REFERENCE : TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 95,122,1988 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 4900 ug/kg SEX/DURATION : female 8 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - other developmental abnormalities REFERENCE : TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 95,122,1988

合成路线

71748-57-7 ~87% 38030-57-8

文献：Mironova; Leont'eva; Shevyakov; Alexeeva; Shvets; Demina; Krasnokutskaya; Finkel'shtein; Khodonov Russian Journal of Bioorganic Chemistry, 2002 , vol. 28, # 6 p. 487 - 493

38030-59-0 ~% 38030-57-8

文献：Rosenberger Journal of Organic Chemistry, 1982 , vol. 47, # 9 p. 1698 - 1701

81121-19-9 ~% 38030-57-8

文献：Rosenberger Journal of Organic Chemistry, 1982 , vol. 47, # 9 p. 1698 - 1701

72526-76-2 ~% 38030-57-8

文献：Aig, Edward; Focella, Antonino; Parrish, David R.; Rosenberger, Michael; Scott, John W.; Zenchoff, Gladys B. Synthetic Communications, 1987 , vol. 17, # 4 p. 419 - 430

63184-93-0 ~% 38030-57-8

文献：Aig, Edward; Focella, Antonino; Parrish, David R.; Rosenberger, Michael; Scott, John W.; Zenchoff, Gladys B. Synthetic Communications, 1987 , vol. 17, # 4 p. 419 - 430

302-79-4 ~% 38030-57-8 66592-72-1

文献：UNIVERSITY OF WASHINGTON Patent: US2008/249042 A1, 2008 ; Location in patent: Page/Page column 2; 27; 29; 31; Sheet 14/24; 24/24 ;

33532-44-4 ~% 38030-57-8

文献：Mironova; Leont'eva; Shevyakov; Alexeeva; Shvets; Demina; Krasnokutskaya; Finkel'shtein; Khodonov Russian Journal of Bioorganic Chemistry, 2002 , vol. 28, # 6 p. 487 - 493

62054-49-3 63184-93-0 ~% 38030-57-8

文献：Rosenberger Journal of Organic Chemistry, 1982 , vol. 47, # 9 p. 1698 - 1701

81121-21-3 ~% 38030-57-8 66592-72-1

文献：Aig, Edward; Focella, Antonino; Parrish, David R.; Rosenberger, Michael; Scott, John W.; Zenchoff, Gladys B. Synthetic Communications, 1987 , vol. 17, # 4 p. 419 - 430

上下游产品

上游产品  9
71748-57-7 38030-59-0 81121-19-9 72526-76-2
63184-93-0 302-79-4 33532-44-4 62054-49-3
81121-21-3
下游产品  1
66592-72-1