13-cis-Retinoic acid 13-顺式视黄酸

CAS 4759-48-2 MFCD00079542

化学结构图

4759-48-2
SMILES: CC1=C(/C=C/C(C)=C/C=C/C(C)=C\C(=O)O)C(C)(C)CCC1

化学属性

Mol. FormulaC20 H28 O2
Mol. Weight300.44
Melting Point174-177°C
Appearance (20天)小鼠，大鼠(mg/kg)：904，901腹腔注射；3389＞4000口服。 黄色或淡橙色结晶性粉末，熔点179-184℃ powder 从异丙醇得到橙红色片状结晶，熔点174～175℃。UV最大吸收：354nm(ε39800)。急性毒性LD 50
Solubilityinsoluble
Boiling Point462.8°C at 760 mmHg
Flash Point350.6°C

别名和识别编码

Chemical Name13-cis-Retinoic acid
MDL NumberMFCD00079542
CAS Number4759-48-2
Synonym (L)-ISOTRETINOIN 13 cis Retinoic Acid 13-CIS-RETINOIC ACID 13-cis-RA 13-cis-Retinoic Acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}
EC Number225-296-0
PubChem Substance ID5282379
Chemical Name Translation13-顺式视黄酸
Merck Number5228
Beilstein Registry Number9(4)2388
Reaxys-RN1885770
Wiswesser Line NotationL6UTJ A1 B1U1Y1&U2U1Y1&U1VQ C1 C1
LabNetwork Molecule IDLN01311301
InChIInChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14-
Canonical SMILESCC1(C)C(/C=C/C(C)=C/C=C/C(C)=C\C(O)=O)=C(C)CCC1
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分类

  • {SNA} Analytical Standards,
  • {SNA} Bioactive Small Molecule Alphabetical Index, Gene Regulation, Gene Regulation and Expression, PPAR and RXR Regulators, R, Vitamin A, Vitamins, 抗肿瘤药物, 生物活性小分子, 癌症研究, 细胞信号转导和神经科学, 细胞生物学, 营养研究
  • {SNA} Additional Standards, Analytical Standards, Chromatography, Pharmaceutical Secondary Standards,
  • {SNA} Analytical Standards, EP Standards, EP Standards I - K, Pharmacopeia Metrological Institutes Standards,
  • {SNA} Bioactive Small Molecule Alphabetical Index, Gene Regulation, Gene Regulation and Expression, PPAR and RXR Regulators, R,

相关文献及参考

  • [2]. Norris, D.A., et al., Isotretinoin produces significant inhibition of monocyte and neutrophil chemotaxis in vivo in patients with cystic acne. J Invest Dermatol, 1987. 89(1): p. 38-43.
  • [3]. Rademaker, M., J.M. Wishart, and N.M. Birchall, Isotretinoin 5 mg daily for low-grade adult acne vulgaris - a placebo-controlled, randomized double-blind study. J Eur Acad Dermatol Venereol, 2013.
  • [4]. Dicken, C.H., Isotretinoin treatment of pityriasis rubra pilaris. J Am Acad Dermatol, 1987. 16(2 Pt 1): p. 297-301.
  • [1]. Thielitz, A. and H. Gollnick, [Isotretinoin. How should it be used?]. Hautarzt, 2013. 64(4): p. 263-8.
  • [1]. Thielitz, A. and H. Gollnick, [Isotretinoin. How should it be used?]. Hautarzt, 2013. 64(4): p. 263-8.
  • [2]. Norris, D.A., et al., Isotretinoin produces significant inhibition of monocyte and neutrophil chemotaxis in vivo in patients with cystic acne. J Invest Dermatol, 1987. 89(1): p. 38-43.
  • [3]. Rademaker, M.,

安全信息

WGK Germany3
RTECSVH6440000
GHS Symbol
Precautionary statements
  • P201 Obtain special instructions before use. 使用前获取专门指示。
  • P202 Do not handle until all safety precautions have been read and understood. 已阅读并理解所有的安全预防措施之前，切勿操作。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
  • P273 Avoid release to the environment. 避免释放到环境中。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P281 Use personal protective equipment as required. 使用所需的个人防护装备。
  • P302+P350
  • P302+P352
  • P302+P352+P332+P313+P362+P364
  • P304+P340
  • P305+P351+P338
  • P305+P351+P338+P337+P313
  • P308+P313
  • P312 Call a POISON CENTER or doctor/physician if you feel unwell. 如果你感觉不适，呼叫解毒中心或医生/医师。
  • P321 Specific treatment (see … on this label). 具体治疗（见本标签上的）。
  • P332+P313
  • P337+P313
  • P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服，清洗后方可重新使用
  • P391 Collect spillage. Hazardous to the aquatic environment 收集对水环境有危害的泄漏物。
  • P403+P233
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Hazard statements
  • H315 Causes skin irritation 会刺激皮肤
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
  • H360 May damage fertility or the unborn child 可能对生育能力或未出生婴儿造成伤害
  • H400 Verytoxictoaquaticlife 对水生生物毒性非常大。
  • H410 Verytoxictoaquaticlifewithlonglastingeffects 对水生生物毒性非常大并具有长期影响。
Signal word Danger
Personal Protective Equipment Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
Safety Statements
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
  • S37/39 Wear suitable gloves and eye/face protection 穿戴适当的手套和眼睛/面保护；
  • S53 Avoid exposure - obtain special instructions before use 避免接触，使用前获得特别指示说明；
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时，立即求医（可能时出示标签）；
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护；
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套；
Hazard Codes T T,Xn
Risk Statements
  • R61 May cause harm to the unborn child 可能对未出生的婴儿导致伤害
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
Packing GroupIII
Hazard Class6.1(b)
Storage condition - 86℃ -20°C -86°C 2-8°C <0°C
UN Number 3249 
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 3389 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   51ZKAN "The Retinoids, Vol.2," Sporn, M.B., et al., eds., New York, Academic
   Press, Inc., 1984  Volume(issue)/page/year: 2,287,1984

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - man
DOSE/DURATION           : 24 mg/kg/4W-I
TOXIC EFFECTS :
   Gastrointestinal - hypermotility, diarrhea
   Gastrointestinal - other changes
REFERENCE :
   GASTAB Gastroenterology.  (Academic Press, Inc., 1 E. First St., Duluth, MN
   55802)  V.1-    1943-  Volume(issue)/page/year: 93,606,1987

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : >4 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   JAADDB Journal of the American Academy of Dermatology.  (C.V. Mosby Co.,
   11830 Westline Industrial Dr., St. Louis, MO 63141)  1979-
   Volume(issue)/page/year: 6,652,1982

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - child
DOSE/DURATION           : 360 mg/kg/26W-I
TOXIC EFFECTS :
   Skin and Appendages - sweating
REFERENCE :
   CUTIBC CUTIS; Cutaneous Medicine for the Practitioner.  (Technical Pub., 875
   Third Ave., New York, NY NY 10022)    1965-  Volume(issue)/page/year:
   38,275,1986

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rabbit
DOSE/DURATION           : 1960 mg/kg
TOXIC EFFECTS :
   Details of toxic effects

TYPE OF TEST            : Mutation test systems - not otherwise specified
TEST SYSTEM             : Human Embryo
DOSE/DURATION           : 25 umol/L
REFERENCE :
   TCMUD8 Teratogenesis, Carcinogenesis, and Mutagenesis.  (Alan R. Liss, Inc.,
   41 E. 11th St., New York, NY 10003)  V.1-    1980- Volume(issue)/page/year:
   11,297,1991

TYPE OF TEST            : Sister chromatid exchange
TEST SYSTEM             : Human Lymphocyte
DOSE/DURATION           : 50 umol/L
REFERENCE :
   BLFSBY Basic Life Sciences.  (Plenum Pub. Corp., 223 Spring St., New York,
   NY 10003)  V.1-    1973-  Volume(issue)/page/year: 29A,333,1984

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 100 mg/kg
SEX/DURATION            : female 10-11 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Fertility - post-implantation mortality (e.g. dead and/or
   resorbed implants per total number of implants)
   Reproductive - Specific Developmental Abnormalities - craniofacial
   (including nose and tongue)
   Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
   IJEPEI International Journal of Experimental Pathology.  (Blackwell
   Scientific Publications Ltd., POB 88, Oxford, OX2 0NE, United kingdom) V.71-
      1990-  Volume(issue)/page/year: 73,551,1992

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - woman
DOSE                    : 2400 ug/kg
SEX/DURATION            : female 22-24 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - Central Nervous System
   Reproductive - Specific Developmental Abnormalities - eye/ear
   Reproductive - Specific Developmental Abnormalities - craniofacial
   (including nose and tongue)
REFERENCE :
   AJOTBN American Journal of Otology.  (J.B. Lippincott Co., 227E. Washington
   Square, Philadelphia, PA 19106)  V.1-    1979-  Volume(issue)/page/year:
   15,400,1994

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - hamster
DOSE                    : 50 mg/kg
SEX/DURATION            : female 8 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - eye/ear
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

其他信息

  • 维 A 酸价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 R0064 视黄酸 Retinoic Acid 1G 1520元 2014/06/02 R0064 视黄酸 Retinoic Acid 5G 4700元 2010/06/21 207340010 维 A 酸 all-trans-Retinoic acid 97% 1 GR 1739元
  • color:yellow
  • 用途一:用于异常型痤疮、鱼鳞病和异常型银屑病
  • 用途二:为维生素A类药物，有强而快抑制皮肤腺细胞的增生和分化过程的功能，对严重节状囊性痤疮有高效。本品肠胃吸收较好，而局部用药无效。用于其它药物治疗无效的严重痤疮、囊肿性痤疮、聚会性痤疮，对酒渣鼻、鱼鳞病、毛囊角化症及毛发红糠疹等皮肤疾患也有一定的效果。
  • 用途三:维生素A酸(ATRA) 是一种维生素A酸受体(RAR)和Retinoid X 受体(RXR)的配体，结合上RAR 和 RXR作为转导因子，调控正常细胞和肿瘤细胞的生长和分化。细胞色素P450 (CYPs) 催化ATRA的羟基化；维生素A酸引导胚胎干细胞(embryonic stem cells) 演变成神经元。
  • 方法一:β-紫罗兰酮和乙基氯化镁反应后，再和三苯膦反应形成三苯基镌盐，然后和环戊烯酮衍生物反应，生成异维A酸及其8Z异构体。 其8Z异构体分离后，经硝酸钯作用异构化为异维A酸。
  • Acros Organics:13-顺式视黄酸(异维A酸) 13-cis-Retinoic acid, 99%(4759-48-2)
  • F:7-8-16-23
  • 用途二:用于异常型痤疮、鱼磷病和异常型银屑病。
  • 异维 A 酸价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2010/06/21 418975000 异维 A 酸 13-cis-Retinoic acid 99% 500 MG 2585元
  • MSDS 信息:3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid(302-79-4).msds
  • Alfa Aesar:视黄酸,98% Retinoic acid, 98%(302-79-4)
  • Acros Organics:全反式维甲酸/视黄酸 all-trans-Retinoic acid, 97%(302-79-4)
  • 上游原料:三苯基膦 --> 紫罗兰酮 --> 乙基氯化镁 --> 环戊烯酮 --> 硝酸钯
  • Sigma Aldrich:302-79-4(sigmaaldrich)
  • MSDS 信息:13-cis-Retinoic acid(4759-48-2).msds
  • 用途三:用于严重痤疮等。
  • MOL 文件:4759-48-2.mol
  • MOL 文件:302-79-4.mol
  • Sigma Aldrich:4759-48-2(sigmaaldrich)
  • TCI Shanghai:视黄酸 Retinoic Acid,>;98.0%(T)(302-79-4)
  • 图谱信息:维 A 酸(302-79-4)红外图谱(IR1)
  • 维 A 酸价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/04/16 R0064 视黄酸 Retinoic Acid 1G 1250元 2011/04/16 R0064 视黄酸 Retinoic Acid 5G 3880元 2010/06/21 207340010 维 A 酸 all-trans-Retinoic acid 97% 1 GR 1739元
  • 用途一:用于治疗严重痤疮等症

系列性分类

  1. Life Science 生命科学
  2. Cancer Research
  3. Antitumor Agents - Cancer Research
  4. Gene Regulation - Antitumor Agents
  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Cell Signaling and Neuroscience - Cell Biology
  4. Gene Regulation and Expression - Cell Signaling and Neuroscience
  5. PPAR and RXR Regulators - Gene Regulation and Expression
  1. Analytical & Chromatography 分析化学与色谱
  2. Analytical Standards
  3. Chromatography - Analytical Standards
  4. Pharmaceutical Standards - Chromatography
  5. Pharmaceutical Secondary Standards - Pharmaceutical Standards
  1. Medical Research Areas
  2. Metabolism
  3. RAR/RXR  (维甲酸受体)
  1. Medical Research Areas
  2. Metabolism
  3. Endogenous Metabolite  (内源性代谢物)

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