56531-55-6

Basic information

• Product Name: 3-(4-HYDROXYPHENYL)ADAMANTANE-1-CARBOXYLIC ACID
• Synonyms: tricyclo[3.3.1.1~3,7~]decane-1-carboxylic acid, 3-(4-hydro;3-(4-hydroxyphenyl)-1-adamantanecarboxylic acid;3-(4-Hydroxyphenyl)adamantanecarboxylic acid;3-(4-Hydroxyphenyl)tricyclo(3.3.1.1(sup 3,7))decane-1-carboxylic acid;Tricyclo(3.3.1.1(sup 3,7))decane-1-carboxylic acid, 3-(4-hydroxyphenyl)-;Tricyclo(3.3.1.1(sup3,7)decane-1-carboxylic acid, 3-(4-hydroxyphenyl)-
• CAS NO: 56531-55-6
• Molecular Formula: C₁₇H₂₀O₃
• Molecular Weight: 272.35
• Mol File: 56531-55-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 461.4°C at 760 mmHg
• Flash Point: 247°C
• Appearance: /
• Density: 1.336g/cm³
• Vapor Pressure: 2.61E-09mmHg at 25°C
• Refractive Index: 1.651
• CAS DataBase Reference: 3-(4-HYDROXYPHENYL)ADAMANTANE-1-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-HYDROXYPHENYL)ADAMANTANE-1-CARBOXYLIC ACID(56531-55-6)
• EPA Substance Registry System: 3-(4-HYDROXYPHENYL)ADAMANTANE-1-CARBOXYLIC ACID(56531-55-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 56531-55-6(Hazardous Substances Data)

Usage

General Description

3-(4-Hydroxyphenyl)adamantane-1-carboxylic acid is a chemical compound with a molecular formula of C20H26O3. It is a derivative of adamantane, which is a rigid polycyclic hydrocarbon. The compound contains a hydroxyphenyl group and a carboxylic acid group, and is often used in the pharmaceutical industry as a building block for the synthesis of various drugs and therapeutic agents. It also exhibits antioxidant and anti-inflammatory properties, making it potentially useful for the development of pharmaceuticals targeted at treating conditions such as neurodegenerative diseases and inflammatory disorders.

InChI:InChI=1/C17H20O3/c18-14-3-1-13(2-4-14)16-6-11-5-12(7-16)9-17(8-11,10-16)15(19)20/h1-4,11-12,18H,5-10H2,(H,19,20)

Upstream product

• 21816-08-0 3-bromoadamantane-1-carboxylic acid 
• 108-95-2 phenol 
• 828-51-3 1-Adamantanecarboxylic acid 
• 100-66-3 methoxybenzene 
• 56531-56-7 3-(4-methoxyphenyl)adamantane-1-carboxylic acid 

Downstream Products

• 126164-66-7 methyl 3-(4-hydroxyphenyl)adamantanecarboxylate 
• 1192322-46-5 3-(4-Hydroxyphenyl)-adamantane-1-carboxylic acid benzyl ester 
• 1192322-49-8 3-(4-ethoxycarbonylmethoxyphenyl)adamantane-1-carboxylic acid benzylester 
• 1192322-53-4 3-(4-[(3-methoxycarbonylphenylcarbamoyl)methoxy]phenyl)adamantane-1-carboxylic acid benzylester 
• 1192322-52-3 3-(4-carboxymethoxyphenyl)adamantane-1-carboxylic acid benzylester 
• 126164-70-3 3-(4-acetoxyphenyl)adamantanecarboxykic acid 2,6-dichlorophenylamide 
• 126164-68-9 3-(4-hydroxyphenyl)adamantanecarboxylic acid 2,6-dichlorophenylamine 
• 126164-67-8 3-(4-hydroxyphenyl)adamantane carboxylic acid hydrazide 
• 126164-69-0 3-(4-acetoxyphenyl)adamantanecarboxylic acid 
• 126145-55-9 3-(4-hydroxy-3iodophenyl)adamantanecarboxylic acid 
• 126145-54-8 3-(3-bromo-4-hydroxyphenyl)adamantanecarboxylic acid 

Relevant articles and documents

Disubstituted adamantyl derivative or pharmaceutically acceptable salt thereof, and pharmaceutical composition and kit for inhibiting the growth of cancer containing the same as an active ingredient

The present invention relates to: a disubstituted adamantyl derivative or a pharmaceutically acceptable salt thereof, and an anticancer pharmaceutical composition and a kit containing same as an active ingredient. The disubstituted adamantyl derivative according to the present invention suppresses the growth of cancer cells by targeting mitochondria ETC complex I and damaging the metabolism of cancer cells, and thus can be useful as an anticancer pharmaceutical composition that is a powerful therapeutic agent for cancer dependent on oxidative phosphorylation for producing ATP.

Synthesis and structure-activity relationship study of chemical probes as hypoxia induced factor-1α/malate dehydrogenase 2 inhibitors

A structure-activity relationship study of hypoxia inducible factor-1α inhibitor 3-aminobenzoic acid-based chemical probes, which were previously identified to bind to mitochondrial malate dehydrogenase 2, was performed to provide a better understanding of the pharmacological effects of LW6 and its relation to hypoxia inducible factor-1α (HIF-1α) and malate dehydrogenase 2 (MDH2). A variety of multifunctional probes including the benzophenone or the trifluoromethyl diazirine for photoaffinity labeling and click reaction were prepared and evaluated for their biological activity using a cell-based HRE-luciferase assay as well as a MDH2 assay in human colorectal cancer HCT116 cells. Among them, the diazirine probe 4a showed strong inhibitory activity against both HIF-1α and MDH2. Significantly, the inhibitory effect of the probes on HIF-1α activity was consistent with that of the MDH2 enzyme assay, which was further confirmed by the effect on in vitro binding activity to recombinant human MDH2, oxygen consumption, ATP production, and AMP activated protein kinase (AMPK) activation. Competitive binding modes of LW6 and probe 4a to MDH2 were also demonstrated.

Synthesis and biological activity of 5-(adamant-1-yl)salicylic acid, 3-(4-hydroxyphenyl)adamantanecarboxylic acid and some of their derivatives

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