all-trans-4-Oxoretinoic acid

Modify Date: 2024-01-02 18:07:07

all-trans-4-Oxoretinoic acid Structure
all-trans-4-Oxoretinoic acid structure
 Common Name all-trans-4-Oxoretinoic acid
CAS Number 38030-57-8 Molecular Weight 314.41900
Density 1.07g/cm3 Boiling Point 509.9ºC at 760 mmHg
Molecular Formula C20H26O3 Melting Point 175-178°C (分解)
MSDS N/A Flash Point 276.3ºC

 Use of all-trans-4-Oxoretinoic acid


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

 Names

Name all-trans-4-oxoretinoic acid
Synonym More Synonyms

 all-trans-4-Oxoretinoic acid 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
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.

 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

4-Keto 13-cis-Retinoic Acid Methyl Ester structure

4-Keto 13-cis-R...

CAS#:71748-57-7

~87%

all-trans-4-Oxoretinoic acid Structure

all-trans-4-Oxo...

CAS#:38030-57-8

Literature: Mironova; Leont'eva; Shevyakov; Alexeeva; Shvets; Demina; Krasnokutskaya; Finkel'shtein; Khodonov Russian Journal of Bioorganic Chemistry, 2002 , vol. 28, # 6 p. 487 - 493
4-Hydroxyretinoic acid methyl ester structure

4-Hydroxyretino...

CAS#:38030-59-0

~%

all-trans-4-Oxoretinoic acid Structure

all-trans-4-Oxo...

CAS#:38030-57-8

Literature: Rosenberger Journal of Organic Chemistry, 1982 , vol. 47, # 9 p. 1698 - 1701
ethyl (2E,4E,6E,8E)-9-(3-acetoxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenoate structure

ethyl (2E,4E,6E...

CAS#:81121-19-9

~%

all-trans-4-Oxoretinoic acid Structure

all-trans-4-Oxo...

CAS#:38030-57-8

Literature: Rosenberger Journal of Organic Chemistry, 1982 , vol. 47, # 9 p. 1698 - 1701
ethyl (2E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate structure

ethyl (2E,6E,8E...

CAS#:72526-76-2

~%

all-trans-4-Oxoretinoic acid Structure

all-trans-4-Oxo...

CAS#:38030-57-8

Literature: Aig, Edward; Focella, Antonino; Parrish, David R.; Rosenberger, Michael; Scott, John W.; Zenchoff, Gladys B. Synthetic Communications, 1987 , vol. 17, # 4 p. 419 - 430
(2E,4E)-[5-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-yl]triphenylphosphonium bromide structure

(2E,4E)-[5-(2,6...

CAS#:63184-93-0

~%

all-trans-4-Oxoretinoic acid Structure

all-trans-4-Oxo...

CAS#:38030-57-8

Literature: Aig, Edward; Focella, Antonino; Parrish, David R.; Rosenberger, Michael; Scott, John W.; Zenchoff, Gladys B. Synthetic Communications, 1987 , vol. 17, # 4 p. 419 - 430
Retinoic acid structure

Retinoic acid

CAS#:302-79-4

~%

all-trans-4-Oxoretinoic acid Structure

all-trans-4-Oxo...

CAS#:38030-57-8

4-Hydroxyretinoic acid structure

4-Hydroxyretino...

CAS#:66592-72-1

Literature: UNIVERSITY OF WASHINGTON Patent: US2008/249042 A1, 2008 ; Location in patent: Page/Page column 2; 27; 29; 31; Sheet 14/24; 24/24 ;
4-oxoretinaldehyde structure

4-oxoretinaldehyde

CAS#:33532-44-4

~%

all-trans-4-Oxoretinoic acid Structure

all-trans-4-Oxo...

CAS#:38030-57-8

Literature: Mironova; Leont'eva; Shevyakov; Alexeeva; Shvets; Demina; Krasnokutskaya; Finkel'shtein; Khodonov Russian Journal of Bioorganic Chemistry, 2002 , vol. 28, # 6 p. 487 - 493
Ethyl (E)-3-methyl-4-oxobut-2-enoate structure

Ethyl (E)-3-met...

CAS#:62054-49-3

(2E,4E)-[5-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-yl]triphenylphosphonium bromide structure

(2E,4E)-[5-(2,6...

CAS#:63184-93-0

~%

all-trans-4-Oxoretinoic acid Structure

all-trans-4-Oxo...

CAS#:38030-57-8

Literature: Rosenberger Journal of Organic Chemistry, 1982 , vol. 47, # 9 p. 1698 - 1701
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 structure

rac-(2E,4E,6E,8...

CAS#:81121-21-3

~%

all-trans-4-Oxoretinoic acid Structure

all-trans-4-Oxo...

CAS#:38030-57-8

4-Hydroxyretinoic acid structure

4-Hydroxyretino...

CAS#:66592-72-1

Literature: Aig, Edward; Focella, Antonino; Parrish, David R.; Rosenberger, Michael; Scott, John W.; Zenchoff, Gladys B. Synthetic Communications, 1987 , vol. 17, # 4 p. 419 - 430

 Synonyms

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
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