77123-17-2

Basic information

• Product Name: (3R,4R)-3,4-dihydrophenanthrene-3,4-diol
• Synonyms: (3R,4R)-3,4-dihydrophenanthrene-3,4-diol
• CAS NO: 77123-17-2
• Molecular Formula: C14H12O2
• Molecular Weight: 212.24
• Mol File: 77123-17-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 435°C at 760 mmHg
• Flash Point: 217.5°C
• Appearance: /
• Density: 1.346g/cm³
• Vapor Pressure: 2.46E-08mmHg at 25°C
• Refractive Index: 1.741
• CAS DataBase Reference: (3R,4R)-3,4-dihydrophenanthrene-3,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4R)-3,4-dihydrophenanthrene-3,4-diol(77123-17-2)
• EPA Substance Registry System: (3R,4R)-3,4-dihydrophenanthrene-3,4-diol(77123-17-2)

Safety Data

• Hazardous Substances Data: 77123-17-2(Hazardous Substances Data)

Usage

Description

(3R,4R)-3,4-dihydrophenanthrene-3,4-diol is a chemical compound belonging to the class of dihydrophenanthrenes, characterized by a phenanthrene ring with two additional hydrogen atoms. This specific enantiomer, distinguished by its (3R,4R) configuration, possesses a molecular formula of C14H14O2 and exhibits unique structural and chemical properties that make it a subject of interest for various applications in organic synthesis, pharmaceutical research, and material development.

Uses

Used in Organic Synthesis:
(3R,4R)-3,4-dihydrophenanthrene-3,4-diol is utilized as an intermediate in the synthesis of more complex organic molecules, taking advantage of its unique structure and reactivity. Its presence in the molecular framework can lead to the development of novel compounds with specific properties and applications.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (3R,4R)-3,4-dihydrophenanthrene-3,4-diol serves as a key building block for the design and development of new drugs. Its unique stereochemistry and functional groups can be exploited to create molecules with enhanced biological activity and selectivity, potentially leading to the discovery of innovative therapeutic agents.
Used in Material Development:
(3R,4R)-3,4-dihydrophenanthrene-3,4-diol may also find application in the development of new materials, such as polymers or other advanced materials, due to its structural characteristics. Its incorporation into these materials could result in unique properties, such as improved stability, enhanced mechanical strength, or specific interactions with other molecules, making it a valuable component in material science research.

InChI:InChI=1/C14H12O2/c15-12-8-7-10-6-5-9-3-1-2-4-11(9)13(10)14(12)16/h1-8,12,14-16H/t12-,14+/m1/s1

Upstream product

• 85-01-8 phenanthrene 

Relevant articles and documents

Analysis of phenanthrene and benzo[ a ]pyrene tetraol enantiomers in human urine: Relevance to the bay region diol epoxide hypothesis of benzo[ a ]pyrene carcinogenesis and to biomarker studies

One widely accepted metabolic activation pathway of the prototypic carcinogenic polycyclic aromatic hydrocarbon (PAH) benzo[a]pyrene (BaP) proceeds through the "bay region diol epoxide" BaP-(7R,8S)-diol-(9S,10R)- epoxide (2). However, few studies have addressed the analysis of human urinary metabolites of BaP, which result from this pathway. Phenanthrene (Phe) is structurally related to BaP, but human exposure to Phe is far greater, and its metabolites can be readily detected in urine. Thus, Phe metabolites have been proposed as biomarkers of PAH exposure and metabolic activation. Phe-tetraols in particular could be biomarkers of the diol epoxide pathway. While BaP-tetraols and Phe-tetraols have been previously quantified in human urine, no published studies have determined their enantiomeric composition. This is important because different enantiomers would result from the bay region diol epoxide and "reverse" diol epoxide pathways, the latter being associated with weak mutagenicity and carcinogenicity. We addressed this problem using chiral HPLC to separate the enantiomers of BaP-7,8,9,10-tetraol and Phe-1,2,3,4-tetraol. Urine samples from smokers were subjected to solid-phase extraction, chiral HPLC, and GC-NICI-MS/MS analysis for silylated Phe-1,2,3,4-tetraols. The results demonstrated that >96% of Phe-1,2,3,4-tetraol in smokers urine was Phe-(1S,2R,3S,4R)-tetraol (12), resulting from the "reverse" diol epoxide pathway, whereas less than 4% resulted from the "bay region diol epoxide" pathway of Phe metabolism. Urine from creosote workers was similarly analyzed for BaP-7,8,9,10-tetraol enantiomers. In contrast to the results of the Phe-tetraol analyses, 78% of BaP-7,8,9,10-tetraol in these human urine samples was BaP-(7R,8S,9R,10S)-tetraol (3) resulting from the "bay region diol epoxide" pathway of BaP metabolism. These results provide further support for the bay region diol epoxide pathway of BaP metabolism in humans and demonstrate differences in BaP and Phe metabolism, which may be important when considering Phe-tetraols as biomarkers of PAH metabolic activation.