<Suppliers Price>

all-trans-4-Oxoretinoic acid

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

Biological Activity

[Description]:

all-trans-4-Oxoretinoic acid, an active metabolite of vitamin A, induces gene transcription via binding to nuclear retinoic acid receptors (RARs).

[Related Catalog]:

Natural Products >> Others
Research Areas >> Metabolic Disease

[Target]

Human Endogenous Metabolite


[In Vitro]

all-trans-4-Oxoretinoic acid, an active metabolite of vitamin A, induces gene transcription via binding to nuclear retinoic acid receptors (RARs)[1]. all-trans-4-Oxoretinoic acid is a biologically active geometric isomer of retinoic acid (RA) [2].

[References]

[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.


[Related Small Molecules]

3-Methyladenine | Hydrocortisone | Acetylcysteine(N-acetylcysteine) | Retinoic acid | Melatonine | Dinoprostone | Nicotinamide | Adenosine triphosphate | 4-Acetamidophenol | Prostaglandin E1 | Dehydroepiandrosterone | Corticosterone | Progesterone | Docosahexaenoic Acid | NAD+

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

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds