4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID

ChemicalBook > CAS DataBase List > 4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID

4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID

Product Name: 4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID
CAS No.: 102121-60-8
Chemical Name: 4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID
Synonyms: cd336;AM 580;CS-1051;l)amino-;ro40-6055;NSC 608001;AM580 (CD336);AM-580;AM 580;CD336; NSC608001; RO 40-6055;4-(1,1,4,4-Tetramethyltetralin-6-ylcarbonylamino)benzoic acid;4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CA...
CBNumber: CB9781234
Molecular Formula: C22H25NO3
Formula Weight: 351.44
MOL File: 102121-60-8.mol

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4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID Property

Melting point:: 265-267℃
Boiling point:: 485.24°C (rough estimate)
Density: 1.154
refractive index: 1.5614 (estimate)
storage temp.: -20°C
solubility: Soluble in DMSO (20mg/ml) or ethanol (10mg/ml).
form: White to off-white solid.
pka: 4.28±0.10(Predicted)
color: Off-white
Stability:: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.

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Safety

WGK Germany: 3
RTECS: DH6834890
HS Code: 2924.29.7790

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: A8843
Product name: AM 580
Purity: ≥98% (HPLC)
Packaging: 5mg
Price: $229
Updated: 2024/03/01

TCI Chemical

Product number: A3082
Product name: AM 580
Packaging: 5MG
Price: $63
Updated: 2024/03/01

TCI Chemical

Product number: A3082
Product name: AM 580
Packaging: 100MG
Price: $516
Updated: 2024/03/01

Alfa Aesar

Product number: J65155
Product name: AM 580
Packaging: 10mg
Price: $131.65
Updated: 2024/03/01

Cayman Chemical

Product number: 15261
Product name: AM 580
Purity: ≥98%
Packaging: 1mg
Price: $32
Updated: 2024/03/01

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4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID Chemical Properties,Usage,Production

Description

AM-580 (102121-60-8) is a retinoic acid analog acting as a RARα agonist (Kd = 8 nM).1 Induces or blocks differentiation depending on cell type and environment.2,3 In combination with CHIR-99021 it induces differentiation of human induced pluripotent stem cells (iPSCs) into intermediate mesoderm (80% induction rate in 5 days) capable of forming kidney structures.4 AM-580 exhibits anti-angiogenic activity in vivo, and induces differentiation of acute promyelocytic leukemia cells.5,6

Uses

Retinoid derivative used for gene expression studies of leukemia-retinoic acid receptor (PHL-RAR) cell line differentiation. AM 580 inhibits tumor proliferation by reducing the level of RARγ and activates RAR β. This receptor increases the expression of disintegrin and metalloprotease.

Definition

ChEBI: An amidobenzoic acid obtained by formal condensation of the carboxy group of (5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)benzoic acid with the anilino group of 4-aminobenzoic acid. A selective RARalpha agonist.

General Description

AM580 is a retinobenzoic derivative and a RAR-α (retinoic acid receptor-α) agonist. It stimulates the maturation of granulocytes in NB4 promyelocytic leukemia cell line and APL (acute promyelocytic leukemia) blasts. AM580 suppresses endometrial cancer cell proliferation.

Biological Activity

An analog of retinoic acid that acts as a selective RAR α agonist (EC 50 values are 0.3, 8.6 and 13 nM for RAR α , RAR β and RAR γ respectively). Significantly induces IL-4, IL-5 and IL-13 and inhibits IL-12 and IFN γ synthesis, and induces cell differentiation with over 7 times the activity of retinoic acid in vitro .

storage

Store at RT

References

Bernard et al. (1992), Identification of synthetic retinoids with selectivity for human nuclear retinoic acid receptor gamma; Biochem. Biophys. Res. Commun. 186 977 Safonova et al. (1994), Fatty acids and retinoids act synergistically on adipose cell differentiation; Biochem. Biophys. Res. Commun. 204 498 Shibuyua et al. (2005), Retinoic acid is a potential negative regulator for differentiation of human periodontal ligament cells; J. Periodontal Res. 40 432 Araoka et al. (2014), Efficient and rapid induction of human iPSCs/ESCs into nephrogenic intermediate mesoderm using small molecule-based differentiation methods; PLoS One. 9 e84881 Oikawa et al. (1993), Three novel synthetic retinoids, Re 80, Am 580 and Am 80, all exhibit anti-angiogenic activity in vivo; Eur. J. Pharmacol.249 113 Gianni et al. (1996), AM580, s stable benzoic acid derivative of retinoic acid has powerful and selective cyto-differentiating effects on acute promyelocytic leukemia cells; Blood 87 1520

4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID Preparation Products And Raw materials

Raw materials

Preparation Products

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102121-60-8, 4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACIDRelated Search:

TCPOBOP Mifepristone Troglitazone Ro 41-5253 4-[2-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)ethynyl)-benzoicacid 4-N-BUTYLBENZYLAMINE 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydronaphthalene 4-N-BUTYLBENZAMIDE 1,1,4,4,6-Pentamethyl-1,2,3,4-tetrahydronaphthalene (5,5,8,8-TETRAMETHYL-5,6,7,8-TETRAHYDRONAPHTH-2-YL)METHYLAMINE 1-(3-tert-butylphenyl)methanamine 4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID 5,5,8,8-TETRAMETHYL-5,6,7,8-TETRAHYDRO-2-NAPHTHALENECARBALDEHYDE N,5,5,8,8-PENTAMETHYL-(5,6,7,8-TETRAHYDRONAPHTH-2-YLMETHYL)AMINE 4-[(4-methylbenzyl)amino]benzoic acid C-(5,6,7,8-TETRAHYDRO-NAPHTHALEN-2-YL)-METHYLAMINE 4-PENTYLBENZYLAMINE 2-(aminopropyl-1-oxyl)-4-((5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carboxamido)benzoic acid

AM 580

4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID

2-Naphthalenecarboxamide,5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-N-3-quinolinyl-

Benzoic acid,4-[[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbonyl]amino]-

4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxamido)benzoic acid

4-((5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbonyl)aminobenz

4-(1,1,4,4-Tetramethyltetralin-6-ylcarbonylamino)benzoic acid

4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-ylcarbonylamino)benzoic acid

4-[[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphthalen)-2-yl]carbonylamino]benzoic acid

4-[[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbonyl]amino]benzoic acid

NSC 608001

4-{[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl]amino}benzoic acid

AM580 (CD336)

benzoicacid,4-((5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbony

cd336

l)amino-

ro40-6055

CS-1051

AM-580;AM 580;CD336; NSC608001; RO 40-6055

4-[(5,5,8,8-tetramethyl-6,7-dihydronaphthalene-2-carbonyl)amino]benzoic acid

4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CA...

inhibit,Inhibitor,NSC-608001,Retinoic acid receptors,CD-336,RAR/RXR,AM 580,CD 336,AM-580,Autophagy,NSC 608001,AM580,Retinoid X receptors

4-((5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carboxamido)benzoi

102121-60-8

PPAR and RXR Regulators

Gene Regulation and Expression

Cell Biology

Cell Signaling and Neuroscience

BioChemical

Intracellular receptor