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;MCE AM580;NSC 608001;AM580 (CD336);AM580, 10 mM in DMSO;AM580, RARalpha agonists
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)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
A8843
Product name
AM 580
Purity
≥98% (HPLC)
Packaging
5mg
Price
$235
Updated
2025/07/31
TCI Chemical
Product number
A3082
Product name
AM 580
Packaging
5MG
Price
$57
Updated
2025/07/31
TCI Chemical
Product number
A3082
Product name
AM 580
Packaging
100MG
Price
$464
Updated
2025/07/31
Cayman Chemical
Product number
15261
Product name
AM 580
Purity
≥98%
Packaging
1mg
Price
$32
Updated
2024/03/01
Cayman Chemical
Product number
15261
Product name
AM 580
Purity
≥98%
Packaging
5mg
Price
$93
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 .

Synthesis

102121-59-5

102121-60-8

To a 25 mL round-bottomed flask equipped with a reflux condenser tube was added methyl 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxamido)benzoate (0.200 g, 0.547 mmol), methanol (10 mL) and potassium hydroxide (0.122 g, 2.18 mmol). The reaction mixture was stirred under reflux conditions for 16 h and subsequently evaporated to dryness. The residue was partitioned between ethyl acetate and deionized water and adjusted to acidic pH with 6 N hydrochloric acid. the organic layer was separated, washed sequentially with deionized water, saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated by rotary evaporation to afford 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxamido)benzoic acid as a white solid (0.151 g, 78% yield ). Molecular weight: 351.43; melting point: 265°C; Rf value: 0.3 (ethyl acetate:cyclohexane=50:50).1H NMR (CDCl3, δ): 1.32 (s, 6H, 2×CH3), 1.34 (s, 6H, 2×CH3), 1.73 (s, 4H, 2×CH2), 7.43 (d, 1H, J=8.53 Hz. ArH), 7.57 (d, 1H, J=8.25 Hz, J=1.98 Hz, ArH), 7.78 (d, 2H, J=8.74 Hz, ArH), 7.88 (d, 1H, J=8.74 Hz, ArH), 7.92 (s, 1H, NH), 8.13 (d, 2H, J=8.70 Hz, ArH), and no observed carboxylic acid proton signal.MS-ESI: m/z (relative intensity) 352.1 ([M+H]+, 100).HPLC analysis (Method A, detection wavelength 254 nm): retention time = 6.66 min, peak area = 96.3%.

storage

Store at RT

References

[1] BRUNO A. BERNARD . Identification of synthetic retinoids with selectivity for human nuclear retinoic acid receptor γ[J]. Biochemical and biophysical research communications, 1992, 186 2: Pages 977-983. DOI:10.1016/0006-291x(92)90842-9
[2] SAFONOVA I. Fatty Acids and Retinoids Act Synergistically on Adipose Cell Differentiation[J]. Biochemical and biophysical research communications, 1994, 204 2: Pages 498-504. DOI:10.1006/bbrc.1994.2487
[3] NATSUKO SHIBUYA. Retinoic acid is a potential negative regulator for differentiation of human periodontal ligament cells[J]. Journal of periodontal research, 2005, 40 6: 432-440. DOI:10.1111/j.1600-0765.2005.00811.x
[4] TOSHIKAZU ARAOKA. Efficient and rapid induction of human iPSCs/ESCs into nephrogenic intermediate mesoderm using small molecule-based differentiation methods.[J]. ACS Applied Bio Materials, 2014: e84881. DOI:10.1371/journal.pone.0084881
[5] TSUTOMU OIKAWA . Three novel synthetic retinoids, Re 80, Am 580 and Am 80, all exhibit anti-angiogenic activity in vivo[J]. European journal of pharmacology, 1993, 249 1: Pages 113-116. DOI:10.1016/0014-2999(93)90669-9
[6] M GIANNÍ. AM580, a stable benzoic derivative of retinoic acid, has powerful and selective cyto-differentiating effects on acute promyelocytic leukemia cells.[J]. Blood, 1996, 87 4: 1520-1531.

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

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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
  • 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
  • AM580, RARalpha agonists
  • AM580, 10 mM in DMSO
  • cd336
  • MCE AM580
  • 102121-60-8
  • PPAR and RXR Regulators
  • Gene Regulation and Expression
  • Cell Biology
  • Cell Signaling and Neuroscience
  • BioChemical
  • Intracellular receptor