Retinoic Acid 视黄酸

CAS 302-79-4 MFCD00001551

化学结构图

302-79-4
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. FormulaC20H28O2
Mol. Weight300.44
Melting Point179-184°C
TSCAYes
SolubilitySoluble in DMSO, not in water
Density1.011
Appearance Solid powder
Boiling Point462.8°C at 760 mmHg

别名和识别编码

Chemical NameRetinoic Acid
CAS Number302-79-4
Alfabeta NameDIMETHYLTRIMETHYLCYCLOHEXENYLNONATETRAENOICACID EEEE2468379266112468(())------------,,,,,,,,,
MDL NumberMFCD00001551
Synonym 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid; all-trans-Retinoic acid; Vitamin A acid Retinoic acid Retinoic acid (Isotretinoin Impurity) {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {MK} alltrans retinoic acid; alltrans vitamin A acid; betaretinoic acid; retinoic acid; TRA; trans retinoic acid; trans vitamin A acid; tretinoinum; Vitamin A Acid. US brand names: Aberel; Aknoten; Avita; Renova; RetinA; RetinA MICRO; Vesanoid. Foreign brand names: Airol; Cordes Vas; Dermairol; EpiAberel; Eudyna; RetisolA; StievaA; StievaA Forte; Vitinoin; ; Abbreviation:
PubChem Substance ID87575622
EC Number206-129-0
Beilstein Registry Number2057223
Merck Number8165
Reaxys-RN2057223
Chemical Name Translation视黄酸
Wiswesser Line NotationL6UTJ A1 B1U1Y1&U2U1Y1&U1VQ C1 C1
LabNetwork Molecule IDLN00176974
FormulaC20H28O2
IUPAC Name(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
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} Antitumor Agents,
  • {SA} Antitumor Agents, Bioactive Small Molecules, Bioactives and Supplements for Stem Cell Expansion, Bioactives/Supplements, Biochemicals and Reagents, Cancer Research, Carotenoid, Cell Biology, Cell Signaling and Neuroscience, Cofactor, Gene Regulation, Gene Regulation and Expression, General Stem Cell Biology, Isoprenoid, Isoprenoids, Lipids, Metabolic Pathways, Metabolites and Cofactors on the Metabolic Pathways Chart, Metabolomics, Nutrition Research, PPAR and RXR Regulators, Phytochemicals by Chemical Classification, Prenols, R,
  • {SNA} Antitumor

产品应用

  • Tretinoin is a naturally-occurring acid of retinol. Tretinoin binds to and activates retinoic acid receptors (RARs), thereby inducing changes in gene expression that lead to cell differentiation, decreased cell proliferation, and inhibition of tumorigenesis. This agent also inhibits telomerase, resulting in telomere shortening and eventual apoptosis of some tumor cell types. The oral form of tretinoin has teratogenic and embryotoxic properties.

相关文献及参考

  • [2]. Shaw N, et al. Retinoic acid is a high affinity selective ligand for the peroxisome proliferator-activated receptor beta/delta. J Biol Chem. 2003 Oct 24;278(43):41589-92.
  • [3]. Yu S, et al. Retinoic acid induces neurogenesis by activating both retinoic acid receptors (RARs) and peroxisomeproliferator-activated receptor β/δ (PPARβ/δ). J Biol Chem. 2012 Dec 7;287(50):42195-205.
  • [4]. Kam RK, et al. Retinoic acid synthesis and functions in early embryonic development. Cell Biosci. 2012 Mar 22;2(1):11.
  • [5]. Apfel C, et al. A retinoic acid receptor alpha antagonist selectively counteracts retinoic acid effects. Proc Natl Acad Sci U S A. 1992 Aug 1;89(15):7129-33.
  • [6]. Xiu Jun Wang, et al. Identification of retinoic acid as an inhibitor of transcription factor Nrf2 through activation of retinoic acid receptor alpha. Proc Natl Acad Sci U S A. 2007 Dec 4;104(49):19589-94.
  • Merck: 14,8165
  • Merck: 14,8165 Beilstein:9(4)2387
  • [1

安全信息

Warnings IRRITANT
GHS Symbol
WGK Germany2
Hazard statements
  • H302 Harmful if swallowed 吞食有害
  • H411 Toxictoaquaticlifewithlonglastingeffects 对水生生物有毒性并具有长期影响。
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
RTECSVH6475000
Signal word Warning
Precautionary statements
  • 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。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西，喝水或吸烟。
  • 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。
  • P301+P312+P330
  • P302+P352+P332+P313+P362+P364
  • P305+P351+P338
  • P305+P351+P338+P337+P313
  • P332+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
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Safety Statements
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触；
Risk Statements
  • R22 Harmful if swallowed 吞咽有害
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
Storage condition -20°C, sealed storage, away from moisture and light Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). Light Sensitive 储存温度：-20°C
Hazard Codes Xn 
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Administration onto the skin
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 8400 mg/kg/30W-I
TOXIC EFFECTS :
   Tumorigenic - neoplastic by RTECS criteria
   Skin and Appendages - photosensitivity (after systemic exposure)
   Skin and Appendages - tumors
REFERENCE :
   CALEDQ Cancer Letters (Shannon, Ireland).  (Elsevier Scientific Pub. Ireland
   Ltd., POB 85, Limerick, Ireland)  V.1-    1975- Volume(issue)/page/year:
   7,85,1979

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : >200 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NIIRDN Drugs in Japan (Ethical Drugs).  (Yakugyo Jiho Co., Ltd., Tokyo,
   Japan)  Volume(issue)/page/year: -,886,1995

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 53 mg/kg
TOXIC EFFECTS :
   Behavioral - hallucinations, distorted perceptions
   Lungs, Thorax, or Respiration - respiratory depression
   Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
   KSRNAM Kiso to Rinsho.  Clinical Report.  (Yubunsha Co., Ltd., 1-5, Kanda
   Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan)  V.1-    1960-
   Volume(issue)/page/year: 7,3194,1973

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DO

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 75 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NIIRDN Drugs in Japan (Ethical Drugs).  (Yakugyo Jiho Co., Ltd., Tokyo,
   Japan)  Volume(issue)/page/year: -,886,1995

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : >500 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NIIRDN Drugs in Japan (Ethical Drugs).  (Yakugyo Jiho Co., Ltd., Tokyo,
   Japan)  Volume(issue)/page/year: -,886,1995

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Rodent - mouse Lymphocyte
DOSE/DURATION           : 1 umol/L
REFERENCE :
   ONCOBS Oncology.  (S. Karger AG, Postfach CH-4009 Basel, Switzerland) V.21- 
     1967-  Volume(issue)/page/year: 44,356,1987

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Human Leukocyte
DOSE/DURATION           : 1 umol/L
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   46,1388,1986

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Rodent - rat Mammary gland
DOSE/DURATION           : 3 umol/L
REFERENCE :
   JJIND8 JNCI, Journal of the National Cancer Institute.  (Washington, DC)
   V.61-79, 1978-87. For publisher information, see

TYPE OF TEST            : Mutation test systems - not otherwise specified
TEST SYSTEM             : Rodent - mouse Embryo
DOSE/DURATION           : 10 umol/L
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   42,4918,1982

TYPE OF TEST            : Unscheduled DNA synthesis
ROUTE OF EXPOSURE       : Administration onto the skin
TEST SYSTEM             : Rodent - mouse
DOSE/DURATION           : 4 umol/kg
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   43,5174,1983

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Microorganism - not otherwise specified
DOSE/DURATION           : 1 umol/L
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   45,2098,1985

TYPE OF TEST

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 20 mg/kg
SEX/DURATION            : female 8 day(s) after conception
TOXIC EFFECTS :
   R

{h

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 16 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: 32,32A,1985

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 5 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 :
   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: 32,87,1985

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 20 mg/kg
SEX/DURATION            : female 8 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - Central Nervous 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: 28,123,1983

其他信息

  • 不溶于水，溶于乙醚、DMSO (25 mg/ml)；微溶于乙醇和氯仿。

系列性分类

  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. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Stem Cell Biology - Cell Biology
  4. Small Molecules for Stem Cell Biology - Stem Cell Biology
  1. Chemical Synthesis 化学合成
  2. Synthetic Reagents 合成试剂
  3. Organic Acids - Synthetic Reagents
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Carbonyl Compounds 羰基化合物
  5. Carboxylic Acids - Carbonyl Compounds
  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. Analytical & Chromatography 分析化学与色谱
  2. Syringes
  3. GC Manual Syringes - Syringes
  4. Liquid sampling - GC Manual Syringes
  5. Standard syringe, 5-500 µL - Liquid sampling
  6. Hamilton Microliter™ Syringes, 700 Series - Standard syringe, 5-500 µL
  7. 700 Series, N (Cemented Needle) - Hamilton Microliter™ Syringes, 700 Series
  1. Life Science 生命科学
  2. Biochemistry / Glyco-Chemistry
  3. Terpenes
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Vitamins
  4. Folic Acid
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Biochemicals Found in Plants
  4. Carbohydrates
  5. Simple sugars
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Cell Signaling and Neuroscience
  4. Gene Regulation and Expression
  5. Gene Regulation
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Metabolomics
  4. Metabolic Pathways
  5. Metabolites and Cofactors on the Metabolic Pathways Chart
  6. Cholesterol
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Nutrition Research
  4. Biochemicals Found in Plants
  5. Carbohydrates
  6. Simple sugars
  1. Medical Research Areas
  2. DNA Damage
  3. Telomerase
  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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