all-trans-4-Oxoretinoic acid

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Names

[ CAS No. ]:
38030-57-8

[ Name ]:
all-trans-4-Oxoretinoic acid

[Synonym ]:
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

Chemical & Physical Properties

[ Density]:
1.07g/cm3

[ Boiling Point ]:
509.9ºC at 760 mmHg

[ Melting Point ]:
175-178°C (分解)

[ Molecular Formula ]:
C20H26O3

[ Molecular Weight ]:
314.41900

[ Flash Point ]:
276.3ºC

[ Exact Mass ]:
314.18800

[ PSA ]:
54.37000

[ LogP ]:
4.78160

[ Index of Refraction ]:
1.565

[ Storage condition ]:
2-8℃

Toxicological Information

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

Synthetic Route

Precursor & DownStream

Precursor

  • 4-Keto 13-cis-Retinoic Acid Methyl Ester
  • 4-Hydroxyretinoic acid methyl ester
  • ethyl (2E,4E,6E,8E)-9-(3-acetoxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenoate
  • ethyl (2E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate
  • (2E,4E)-[5-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-yl]triphenylphosphonium bromide
  • Retinoic acid
  • 4-oxoretinaldehyde
  • Ethyl (E)-3-methyl-4-oxobut-2-enoate
  • rac-(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-hydroxy-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid ethyl ester

DownStream

  • 4-Hydroxyretinoic acid

Related Compounds

  • all-trans-4-oxoretinoic acid
  • all-trans-4-oxoretinoic acid
  • 4-Hydroxyretinoic acid
  • all-trans 4-acetoxyretinal
  • all-trans 4-Hydroxyretinal
  • 4-Keto 13-cis-Retinoic Acid Methyl Ester