CAS 71441-28-6|TTNPB

Introduction：Basic information about CAS 71441-28-6|TTNPB, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. TTNPB BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Articles39
7. Synonyms

Common Name	TTNPB
CAS Number	71441-28-6	Molecular Weight	348.478
Density	1.1±0.1 g/cm3	Boiling Point	486.8±44.0 °C at 760 mmHg
Molecular Formula	C₂₄H₂₈O₂	Melting Point	/
MSDS	ChineseUSA	Flash Point	228.6±23.1 °C
Symbol	GHS07, GHS08	Signal Word	Danger

Names

Name	arotinoid acid
Synonym	More Synonyms

TTNPB BiologicalActivity

Description	TTNPB is a highly potent RAR agonist. Competitive binding assays using human RARs yield IC50s of α=5.1 nM, β= 4.5 nM, and γ=9.3 nM, respectively.
Related Catalog	Signaling Pathways >>Metabolic Enzyme/Protease >>RAR/RXRResearch Areas >>Cancer
Target	IC50: 5.1 nM (RARα), 4.5 nM (RARβ), 9.3 nM (RARγ)[1]
In Vitro	TTNPB inhibits binding of [3H]tRA with IC50s of 3.8 nM, 4 nM, and 4.5 nM for human RARα, β, and γ, respectively. TTNPB competes for [3H]tRA binding to CRABPI with IC50s of 1800 nM[1].
Kinase Assay	Labeled and unlabeled retinoids are added to nucleosol or cytosolic fractions in ethanol so that the total amount of ethanol added is constant in all tubes and did not exceed 2% of the incubation volume. The receptor preparations are incubated with retinoids at 47°C for 4-6 hr. Sephadex PD-10 desalting columns are used to separate bound radioligand from free radioligand after equilibrium is achieved. For competitive binding assays, varying concentrations of unlabeled competing ligand are incubated with the appropriate nucleosol or cytosol in the presence of a fixed concentration of [3H]tRA (sp act. 49.3 Ci/mmol) or [3H]9-cis RA (sp. act. 24.0 Ci/mmol). Final concentrations of [3H] tRA and [3H]9-cis RA for nuclear receptor binding assays are 5nM. Final concentrations of [3H]tRA for CRABP binding assays is 30 nM. The IC50s are calculated. For saturation kinetics, increasing concentrations of radiolabeled ligand ([3H]tRA sp. act. 49.3 Ci/mmol, [3H]TTNPB sp. act. 5.5 Ci/mmol) are added to the nucleosol of the appropriate receptor subtype in the presence (nonspecific binding) or absence (total binding) of a 100-fold molar excess of the corresponding unlabeled retinoid. Specific binding is defined as the total binding minus nonspecific binding. Saturation kinetics are calculated[1].
References	[1]. Pignatello MA, et al. Multiple factors contribute to the toxicity of the aromatic retinoid, TTNPB (Ro 13-7410): binding affinities and disposition. Toxicol Appl Pharmacol. 1997 Feb;142(2):319-27.

Chemical & Physical Properties

Density	1.1±0.1 g/cm3
Boiling Point	486.8±44.0 °C at 760 mmHg
Molecular Formula	C₂₄H₂₈O₂
Molecular Weight	348.478
Flash Point	228.6±23.1 °C
Exact Mass	348.208923
PSA	37.30000
LogP	8.62
Vapour Pressure	0.0±1.3 mmHg at 25°C
Index of Refraction	1.579
InChIKey	FOIVPCKZDPCJJY-JQIJEIRASA-N
SMILES	CC(=Cc1ccc(C(=O)O)cc1)c1ccc2c(c1)C(C)(C)CCC2(C)C
Storage condition	−20°C
Water Solubility	chloroform/methanol: soluble9.80 - 10.20 mg/mL, clear, colorless to light yellow

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DH6834900

CHEMICAL NAME :: Benzoic acid, 4-(2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphth alenyl)-1-propenyl)-, (E)-

CAS REGISTRY NUMBER :: 71441-28-6

LAST UPDATED :: 199806

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C24-H28-O2

MOLECULAR WEIGHT :: 348.52

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1040 ug/kg/4D-I

TOXIC EFFECTS :: Skin and Appendages - dermatitis, other (after systemic exposure) Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 138,169,1996

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1250 ug/kg/25D-I

TOXIC EFFECTS :: Musculoskeletal - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 40,3567,1997

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 125 ug/kg/5D-I

TOXIC EFFECTS :: Endocrine - changes in spleen weight Skin and Appendages - dermatitis, other (after systemic exposure) Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 138,169,1996

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Implant

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 392 ug/kg/14D-I

TOXIC EFFECTS :: Musculoskeletal - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

REFERENCE :: FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 34,91,1996 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 30 ug/kg

SEX/DURATION :: female 9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

REFERENCE :: ARTODN Archives of Toxicology. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.32- 1974- Volume(issue)/page/year: 64,43,1990

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 100 ug/kg

SEX/DURATION :: female 9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

REFERENCE :: ARTODN Archives of Toxicology. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.32- 1974- Volume(issue)/page/year: 64,43,1990

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 37 ug/kg

SEX/DURATION :: female 8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: JJIND8 JNCI, Journal of the National Cancer Institute. (Washington, DC) V.61-79, 1978-87. For publisher information, see JNCIEQ. Volume(issue)/page/year: 78,533,1987

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 75 ug/kg

SEX/DURATION :: female 8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System

REFERENCE :: JJIND8 JNCI, Journal of the National Cancer Institute. (Washington, DC) V.61-79, 1978-87. For publisher information, see JNCIEQ. Volume(issue)/page/year: 78,533,1987

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 290 ug/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 :: JJIND8 JNCI, Journal of the National Cancer Institute. (Washington, DC) V.61-79, 1978-87. For publisher information, see JNCIEQ. Volume(issue)/page/year: 78,533,1987

Safety Information

Symbol	GHS07, GHS08
Signal Word	Danger
Hazard Statements	H315-H319-H335-H360
Precautionary Statements	P201-P261-P305 + P351 + P338-P308 + P313
Personal Protective Equipment	Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes	T: Toxic;
Risk Phrases	R60
Safety Phrases	53-26-36/37/39-45
RIDADR	NONH for all modes of transport
WGK Germany	3
RTECS	DH6834900

Articles39

Retinoids Bias Integrin Expression and Function in Cutaneous T-Cell Lymphoma.

J. Invest. Dermatol. 135 , 2102-8, (2015)

Cutaneous T-cell lymphoma (CTCL) is a heterogeneous group of malignancies characterized by accumulation of malignant T-cells within the skin. Retinoids, metabolic derivatives, and synthetic analogs of...

Additive Effects of Retinoic Acid (RA) and Bone Morphogenetic Protein 4 (BMP-4) Apoptosis Signaling in Retinoblastoma Cell Lines.

PLoS ONE 10 , e0131467, (2015)

Retinoids have been shown to serve promising therapeutic agents for human cancers, e.g. the treatment of neuroblastoma. Synthetic retinoids, specific for particular retinoic acid (RA) receptors, are t...

The bioactive lipid 4-hydroxyphenyl retinamide inhibits flavivirus replication.

Antimicrob. Agents Chemother. 59(1) , 85-95, (2014)

Dengue virus (DENV), a member of the Flaviviridae family, is a mosquito-borne pathogen and the cause of dengue fever. The increasing prevalence of DENV worldwide heightens the need for an effective va...

Synonyms

Ro 13-7410

Arotinoid Acid

MFCD00673917

4-[(1E)-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)-1-propen-1yl]benzoic acid

TTNPB

Tocris-0761

Arotinoic acid

TTNPB (Arotinoid Acid)

4-[(1E)-2-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)-1-propen-1-yl]benzoic acid

(E)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propenyl]benzoic acid

4-[(1E)-2-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-1-en-1-yl]benzoic acid

Lopac-T-3757

4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)propen-1-yl] benzoic acid

4-[(E)-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-1-enyl]benzoic acid

Benzoic acid, 4-[(1E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propen-1-yl]-

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