Arotinoid acid
Basic information
- CAS
71441-28-6- Standard SMILES
C/C(=C\c1ccc(C(=O)O)cc1)c1ccc2c(c1)C(C)(C)CCC2(C)C- InChIKey
FOIVPCKZDPCJJY-JQIJEIRASA-N- Molecular formula
- C24H28O2
- Average molar mass
- 348.5 g/mol
- Monoisotopic mass
- 348.20893013
Overview
Arotinoid acid is a retinoid that consists of benzoic acid substituted at position 4 by a 2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-1-en-1-yl group. It is a synthetic retinoid that acts as a selective agonist for the retinoic acid receptors (RAR). It has a role as an antineoplastic agent, a teratogenic agent and a retinoic acid receptor agonist. It is a member of benzoic acids, a member of naphthalenes and a retinoid.
Names & identifiers
- Preferred name
- Arotinoid acid
- IUPAC
- 4-[(E)-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-1-enyl]benzoic acid
- English name
- TTNPB (Arotinoid Acid)
- Molecular formula
- C24H28O2
- Molecular weight
- 348.48
Names & synonyms
TTNPB71441-28-6Arotinoid acidArotinoic acidRo 13-7410AGN-1911834-[(E)-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-1-enyl]benzoic acid673M8C29UR(E)-4-(2-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propen-1-yl)benzoic acid4-[(1E)-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-1-en-1-yl]benzoic acidCHEBI:75261Ro-137410
Show more names
CS-1005(e)-openyl)arotinoicacidyl)benzoicacid4-[(E)-2-(1,1,4,4T3757 TTNPB[T3757]
4-((E)-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-1-enyl)benzoic acid4-((1E)-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-1-en-1-yl)benzoic acidRefChem:560032622-084-3CCRIS 3297TTNPB (Arotinoid Acid)MFCD00673917DTXSID6040743
Database identifiers
- CAS
71441-28-6
Properties
Computed structural properties
- XLogP
- 7.5
- Topological polar surface area
- 37.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 3
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 549
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point240-241 °C
Physicochemical properties
- Melting point
- 242 °C · 242 °C
- Boiling point
- 422.83 °C · 422.83°C (rough estimate)
- Density
- 1.0932 · 1.0932 (rough estimate)
- refractive index
- 1.448 · 1.4480 (estimate)
- storage temp.
- -20 °C · -20°C
- solubility
- 9.8 · chloroform/methanol: soluble9.80 - 10.20 mg/mL, clear, colorless to light yellow
- form
- White solid
- pka
- 4.28 · 4.28±0.10(Predicted)
- color
- White to Almost white
- InChI
- InChI=1S/C24H28O2/c1-16(14-17-6-8-18(9-7-17)22(25)26)19-10-11-20-21(15-19)24(4,5)13-12-23(20,2)3/h6-11,14-15H,12-13H2,1-5H3,(H,25,26)/b16-14+
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P203, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- rtecs
- DH6834900
- hs_code
- 2916.39.7900
- risk_code
- 60-61-36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- T
- safety_code
- 53-26-36/37/39-45
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335-H360
- Hazard Classifications
- Eye Irrit. 2Repr. 1BSkin Irrit. 2STOT SE 3
Chemistry & industry
Applications
DescriptionTTNPB (Arotinoid Acid) is a potent RAR agonist, and inhibits binding of [3H]tRA with IC50 of 5.1 nM, 4.5 nM, and 9.3 nM for human RARα, β, and γ, respectively.
UsesTTNPB is an analog of retinoic acid that potently and selectively activates retinoic acid receptors (RAR; EC50 = 21, 4, and 2.4 nM for RARα, RARβ, and RARγ, respectively; Beard et al.; Wong et al.). TTNPB has been used for transcriptional assays in 293T cells. It has also been used as a RAR-agonist in cultured human cord blood CD34+CD38-lin- cells. It does not act on retinoid X receptors and weakly agonizes farnesoid X receptor (EC50 > 1 µM). TTNPB is used to study RAR action in diverse processes, including epidermal cell proliferation, embryogenesis, and stem cell differentiation.
UsesTTNPB is an analog of retinoic acid that potently and selectively activates retinoic acid receptors.
Upstream & downstream products
Upstream raw materials
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