CAS 302-79-4 MFCD00001551-Retinoic Acid 视黄酸 TAO{mole}

Retinoic Acid 视黄酸

CAS 302-79-4 MFCD00001551

化学结构图

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. Formula	C20H28O2
Mol. Weight	300.44
Melting Point	179-184°C
TSCA	Yes
Solubility	Soluble in DMSO, not in water
Density	1.011
Appearance	Solid powder
Boiling Point	462.8°C at 760 mmHg

别名和识别编码

Chemical Name	Retinoic Acid
CAS Number	302-79-4
Alfabeta Name	DIMETHYLTRIMETHYLCYCLOHEXENYLNONATETRAENOICACID EEEE2468379266112468(())------------,,,,,,,,,
MDL Number	MFCD00001551
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 ID	87575622
EC Number	206-129-0
Beilstein Registry Number	2057223
Merck Number	8165
Reaxys-RN	2057223
Chemical Name Translation	视黄酸
Wiswesser Line Notation	L6UTJ A1 B1U1Y1&U2U1Y1&U1VQ C1 C1
LabNetwork Molecule ID	LN00176974
Formula	C20H28O2
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 SMILES	CC1(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.

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

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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。