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302-79-4 (Retinoic acid)

1

Identification

Retinoic acid Retinoic acid
Name Retinoic acid
Formula C20H28O2
MW 300.44
CAS No. 302-79-4
EINECS 206-129-0
Smiles CC1(C)C(/C=C/C(C)=C/C=C/C(C)=C/C(O)=O)=C(C)CCC1
Synonyms 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; (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
InChI InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+
2

Introduction

All-trans retinoic acid (ATRA; Vitamin A acid) has been widely investigated for treatments of many cancers including prostate cancer. IC50 Value: Target: RAR in vitro: ATRA was able to induce the growth arrest and to increase HOXB13 expression in AR?prostate cancer cells.

Background Information

Tretinoin is most commonly used as a form of acne treatment. It was the first retinoid developed for this type of topical use. Tretinoin is the best studied retinoid in the treatment of photoaging. It is used by some as a hair loss treatment ......by AOBIOUS INC
All-trans retinoic acid (ATRA; Vitamin A acid) has been widely investigated for treatments of many cancers including prostate cancer. ......by AbMole BioScience
Tretinoin is an endogenous agonist for retinoic acid receptors with IC50 value of 14 nM for RAR-alpha, RAR-beta and RAR-gamma receptors). ......by AdooQ BioScience, LLC
Tretinoin, which is a ligand for both the retinoic acid receptor (RAR) and the retinoid X receptor (RXR), can induce granulocytic differentiation and apoptosis in acute promyelocytic leukemia (APL) cells. ......by BOC Sciences
Retinoic acid is a metabolite of vitamin A that acts as a ligand for both the retinoic acid receptor (RAR) and the retinoid X receptor (RXR). RAR and RXR heterodimerize and act as ligand-dependent transcriptional regulators, with roles in development, reproduction, immunity, organogenesis, and cancer. Retinoic acid primes embryonic stem cells to become neurons. ......by BioVision, Inc.,
Retinoic acid is a natural agonist of RAR nuclear receptors, with IC50s of 14 nM for RARα/β/γ. Retinoic acid also bind to PPARβ/δ, with Kd of 17 nM. ......by MedChemexpress Co., Ltd.
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. ......by MedKoo Biosciences, Inc.
Tretinoin, which is a ligand for both the retinoic acid receptor (RAR) and the retinoid X receptor (RXR), can induce granulocytic differentiation and apoptosis in acute promyelocytic leukemia (APL) cells. ......by Selleck Chemicals LLC
An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE). ......by Target Molecule Corp.
Endogenous agonist for retinoic acid receptors (IC50 = 14 nM for RARα, RARβ and RARγ receptors). Also promotes differentiation of mouse embryonic stem cells (ESCs) into adipocytes, neurons and glia in vitro. Proposed ligand of RORβ (Kd = 280 nM). Activates autophagy. ......by Tocris Bioscience Inc.
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Protocol(Only for Reference)

Cell Experiment

Animal Experiment

4

Physical and Chemical Properties

Appearance:Light yellow to yellow solid EBNumber:EB000023073

Storage condition

Solubility

DMSO by MedChemexpress Co., Ltd.
(25°C) * In vitro DMSO 60 mg/mL (199.73 mM); Ethanol6 mg/mL (19.97 mM); Water<1 mg/mL (<1 mM) by Selleck Chemicals LLC
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Mechanism and Indication

Signaling Pathways NF-κB Metabolic Enzyme/Protease Cell Cycle/DNA Damage
Target RAR/RXR PPAR
Research Area Cancer
Indications
6

Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase
Retinoic acid - Launched
7

Safety Data of Retinoic acid

Hazard Symbols : Xn
Risk Statements : R22;R38;R63
Safety Statements : S36/37;S45
RTECS : VH6475000
WGKGermany : 3
8

Spectral Information

9

Suppliers List

Company Price and Availability Country/Region
AOBIOUS INC USA
AbMole BioScience USA
Abcam 50mg/USD39() USA
AdooQ BioScience, LLC USA
Alfa Aesar. 100mg/USD29() USA
Alfa Chemistry USA
Ark Pharm, Inc. USA
Astatech, Inc. USA
BOC Sciences
Beijing Brilliance Biochemical Co., Ltd. China
BioVision, Inc., 250mg/USD265() USA
Biochempartner Co., Ltd China
CHEMSCENE, LLC 100mg/USD60();500mg/USD78() USA
Carbosynth Limited 10g/USD60()
Cayman Chemical Company 50mg/USD28() USA
Chongqing Huapont Pharm. Co., Ltd. China
Citiwell Corporation Limited China
EMD Millipore 500mg/USD82() USA
Hande Pharma Limited China
MedChemexpress Co., Ltd. 100mg/USD60();500mg/USD78() USA
MedKoo Biosciences, Inc. USA
Nexchem Pharmaceutical Co., Ltd. China
Santa Cruz Biotechnology, Inc. 500mg/USD59() USA
Selleck Chemicals LLC 50mg/USD97(In stock);10mM/1mLIn DMSO/USD130(In stock);10mM(in 1mL DMSO)/USD130(in 1mL DMSO) USA
Shaanxi Pioneer Biotech Co., Ltd. China
Shanghai Chely Co., Ltd. China
Shanghai Haoyuan Chemexpress Co., Ltd. 100mg/USD60();500mg/USD78() China
Shanghai Orient Chemical Co., Ltd. China
Sigma-Aldrich, Inc. 50mg/USD33() USA
Sinova Corporation USA
Taizhou Hengfeng Pharmaceutical & Chemical Co., Ltd. China
Target Molecule Corp. 2mg/USD20();10mg/USD40();50mg/USD98();200mg/USD122() USA
Tocris Bioscience Inc. 50mg/USD75() USA
Tokyo Chemical Industry Co., Ltd. 1g/USD120() Japan
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Related Products

Other Forms of 302-79-4

Name CAS No Formula MW

Recommended Compounds in RAR/RXR PPAR

Name CAS No Formula MW
AGN 205728 859498-05-8 C29H27NO3 437.53
AGN 196996 958295-17-5 C24H20BrNO5 482.32
AGN 194310 229961-45-9 C28H24O2S 424.55
Acitretin (sodium) 925701-88-8 C21H25NaO3 348.41
Acitretin 55079-83-9 C21H26O3 326.43
Adapalene (sodium salt) 911110-93-5 C28H27NaO3 434.5
Adapalene 106685-40-9 C28H28O3 412.52
TTNPB 71441-28-6 C24H28O2 348.48
Magnolol 528-43-8 C18H18O2 266.33
Tazarotene 118292-40-3 C21H21NO2S 351.46
Fenretinide 65646-68-6 C26H33NO2 391.55
LG 100268 153559-76-3 C24H29NO2 363.49
Isotretinoin 4759-48-2 C20H28O2 300.44
Palovarotene 410528-02-8 C27H30N2O2 414.54
AM580 102121-60-8 C22H25NO3 351.44
(R)-Flurbiprofen 51543-40-9 C15H13FO2 244.2609
Tamibarotene 94497-51-5 C22H25NO3 351.44
Bexarotene 153559-49-0 C24H28O2 348.48
AGN 195183 367273-07-2 C22H22ClF2NO4 437.86
AR7 80306-38-3 C15H12ClNO 0.0

Recommended Compounds in Same Indication

Name CAS No Formula MW
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Route of Synthesis

12

References

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More Information

Retinoic acid

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