1,2-dihydroxy-1,2-dihydronaphthalene profile

## 1,2-Dihydroxy-1,2-dihydronaphthalene: A Key Intermediate in Research

**1,2-Dihydroxy-1,2-dihydronaphthalene** (also known as **1,2-naphthalenediol**) is an organic compound with the molecular formula C₁₀H₈O₂. It's a colorless to pale yellow solid that's relatively unstable and readily oxidizes in air.

**Why is it important for research?**

This compound is a crucial intermediate in several research areas, including:

* **Organic synthesis:** 1,2-dihydroxy-1,2-dihydronaphthalene acts as a building block for synthesizing other valuable compounds. Its dihydroxylated structure allows for various reactions, including oxidation, reduction, and functionalization, leading to diverse derivatives.
* **Biochemistry:** The compound is involved in the biosynthesis of certain natural products, including naphthoquinones and related compounds. These compounds exhibit significant biological activity, including antibacterial, antiviral, and anticancer properties.
* **Materials science:** 1,2-dihydroxy-1,2-dihydronaphthalene is used in the synthesis of polymers and other materials with unique properties. Its aromatic structure and reactive functionalities contribute to the development of new materials with applications in electronics, optics, and energy storage.
* **Pharmacology:** This compound's potential as a therapeutic agent is being investigated. Research suggests it may possess anti-inflammatory and antioxidant properties, making it relevant to the treatment of various diseases.

**Specific research areas where it's used:**

* **Synthesis of naphthazarin:** 1,2-dihydroxy-1,2-dihydronaphthalene is a key precursor in the synthesis of naphthazarin, a natural pigment found in fungi. Naphthazarin has been studied for its potential anticancer and antimicrobial properties.
* **Development of novel anti-infective agents:** This compound's dihydroxylated structure makes it a promising starting point for developing new anti-infective agents targeting bacterial or viral infections.
* **Investigation of its potential in cancer therapy:** Research is underway to explore 1,2-dihydroxy-1,2-dihydronaphthalene's potential as an anticancer agent, particularly against leukemia and other cancer types.

**Conclusion:**

1,2-Dihydroxy-1,2-dihydronaphthalene is a versatile compound with broad applications in organic synthesis, biochemistry, materials science, and pharmacology. Its unique structure and reactivity make it a valuable tool for researchers in diverse fields. Continued research into this compound holds promise for developing new technologies and treatments for various diseases.

1,2-dihydroxy-1,2-dihydronaphthalene: naphthalene metabolite; RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

1,2-dihydronaphthalene-1,2-diol : A member of the class of naphthalenediols that is 1,2-dihydronaphthalene substituted by hydroxy groups at positions 1 and 2 respectively. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

ID Source	ID
PubMed CID	362
CHEBI ID	28516
SCHEMBL ID	381084
MeSH ID	M0125082

Synonym
1,2-dihydroxy-1,2-dihydronaphthalene
7234-04-0
CHEBI:28516
1,2-naphthalenediol, 1,2-dihydro-
naphthalene-1,2-dihydrodiol
1,2-dihydronaphthalene-1,2-diol
C06205
FT-0667106
FT-0694300
AKOS006228682
1,2-dihydro-1,2-dihydroxynaphthalene
SCHEMBL381084
(+)-cis-1(r),2(s)-1,2-dihydroxy-1,2-dihydronaphthalene
syn-1,2-dihydro-1,2-naphthalenediol
(-)-(1s,2r)-1,2-dihydro-1,2-naphthalenediol
FT-0772489
Q27103750
DTXSID201291284
PD036527

Excerpt	Reference	Relevance
" Although the nature of the oil does have a deep effect on the phase behavior of the micellar systems, in the present investigation no differences in the yields and in the rates of product formation of the enzymatic system were observed on changing the oil, thus showing that in this case the substrate concentration or bioavailability is not the rate-limiting step."	( Direct micellar systems as a tool to improve the efficiency of aromatic substrate conversion for fine chemicals production. Baglioni, P; Berti, D; Bestetti, G; Briganti, F; Di Gennaro, P; Galli, E; Randazzo, D; Scozzafava, A, 2000)	0.31

Role	Description
bacterial xenobiotic metabolite	Any bacterial metabolite produced by metabolism of a xenobiotic compound in bacteria.
mouse metabolite	Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Class	Description
naphthalenediols	Any hydroxynaphthalene derivative that has two hydroxy substituents.
dihydronaphthalenes	Any carbobycyclic compound that is a dihydronaphthalene or a compound obtained from a dihydronaphthalene by formal substitution of one or more hydrogens.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	2 (15.38)	18.7374
1990's	5 (38.46)	18.2507
2000's	4 (30.77)	29.6817
2010's	1 (7.69)	24.3611
2020's	1 (7.69)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	14 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
catechol [no description available]	2.05	1	catechols	allelochemical; genotoxin; plant metabolite
indole [no description available]	1.99	1	indole; polycyclic heteroarene	Escherichia coli metabolite
naphthalene [no description available]	2.4	2	naphthalenes; ortho-fused bicyclic arene	apoptosis inhibitor; carcinogenic agent; environmental contaminant; mouse metabolite; plant metabolite; volatile oil component
toluene methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.	1.99	1	methylbenzene; toluenes; volatile organic compound	cholinergic antagonist; fuel additive; neurotoxin; non-polar solvent
ponalrestat [no description available]	2	1	phthalazines
9,10-dimethyl-1,2-benzanthracene 9,10-Dimethyl-1,2-benzanthracene: Polycyclic aromatic hydrocarbon found in tobacco smoke that is a potent carcinogen.. 7,12-dimethyltetraphene : A tetraphene having methyl substituents at the 7- and 12-positions. It is a potent carcinogen and is present in tobacco smoke.	2.01	1	ortho-fused polycyclic arene; tetraphenes	carcinogenic agent
2-nitrotoluene nitrotoluene : Any member of the class of toluenes bearing one or more nitro substituents on the benzene ring.	1.99	1	mononitrotoluene	carcinogenic agent; environmental contaminant
salicylaldehyde o-hydroxybenzaldehyde: structure in first source	2.05	1	hydroxybenzaldehyde	nematicide; plant metabolite
1-naphthol 1-naphthol: RN given refers to parent cpd. 1-naphthol : A naphthol carrying a hydroxy group at position 1.. hydroxynaphthalene : Any member of the class of naphthalenes that is naphthalene carrying one or more hydroxy groups.	2.05	1	naphthol	genotoxin; human xenobiotic metabolite
2,4-dinitrotoluene 2,4-dinitrotoluene : A dinitrotoluene in which the methyl group is ortho to one of the nitro groups and para to the other. It is the most common isomer of dinitrotoluene.	1.99	1	dinitrotoluene
2-naphthol 2-naphthol: RN given refers to parent cpd. 2-naphthol : A naphthol carrying a hydroxy group at position 2.. naphthols : Any hydroxynaphthalene derivative that has a single hydroxy substituent.	3.94	13	naphthol	antinematodal drug; genotoxin; human urinary metabolite; human xenobiotic metabolite; mouse metabolite; radical scavenger
catechin Catechin: An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.. catechin : Members of the class of hydroxyflavan that have a flavan-3-ol skeleton and its substituted derivatives.. rac-catechin : A racemate comprising equimolar amounts of (+)- and (-)-catechin. (+)-catechin : The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.	2.02	1	catechin	antioxidant; plant metabolite
benzoxazoles 1,3-benzoxazole : A benzoxazole in which the benzene ring is fused to a 1,3-oxazole ring across positions 4 and 5.. benzoxazole : Compounds based on a fused 1,2- or 1,3-oxazole and benzene bicyclic ring skeleton.	2.25	1	1,3-benzoxazoles; mancude organic heterobicyclic parent
thiazoles [no description available]	2.02	1	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
hydantoins Hydantoins: Compounds based on imidazolidine dione. Some derivatives are ANTICONVULSANTS.. imidazolidine-2,4-dione : An imidazolidinone with oxo groups at position 2 and 4.	2.4	2	imidazolidine-2,4-dione
1,2-naphthoquinone naphthalene-1,2-dione: structure given in first source. 1,2-naphthoquinone : The parent structure of the family of 1,2-naphthoquinones, in which the oxo groups of the quinone moiety are at positions 1 and 2 of the naphthalene ring. It is a metabolite of naphthalene and is found in diesel exhaust particles.	2.69	3	1,2-naphthoquinones	aryl hydrocarbon receptor agonist; carcinogenic agent
1,2-dihydroxynaphthalene 1,2-dihydroxynaphthalene: RN given refers to parent cpd	2	1	naphthalenediol	mouse metabolite
fluorine Fluorine: A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries.	1.96	1	diatomic fluorine; gas molecular entity	NMR chemical shift reference compound
benzo(a)pyrene 7,8-dihydrodiol benzo(a)pyrene 7,8-dihydrodiol: RN given refers to cpd without isomeric designation	2.01	1	pyrenes
tolrestat tolrestat: RN & structure given in first source	2	1	naphthalenes	EC 1.1.1.21 (aldehyde reductase) inhibitor
thiazolyl blue thiazolyl blue: RN & II refers to bromide. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide : The bromide salt of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium.	2.02	1	organic bromide salt	colorimetric reagent; dye
epigallocatechin gallate epigallocatechin gallate: a steroid 5alpha-reductase inhibitor and antimutagen in green tea (Camellia sinensis). (-)-epigallocatechin 3-gallate : A gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin.	2.02	1	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
imirestat imirestat: structure given in first source	2.4	2
benzo(a)pyrene-7,8-dione benzo(a)pyrene-7,8-dione: a metabolite of benzo(a)pyrene; structure given in first source. benzo[a]pyrene-7,8-dione : An o-quinone resulting from the formal oxidation of both of the hydroxy groups of benzo[a]pyrene-cis-7,8-dihydrodiol. Benzo[a]pyrene-7,8-dione is a metabolite of the widespread carcinogen benzo[a]pyrene.	2.01	1	orthoquinones; pyrenes	genotoxin; xenobiotic metabolite
sorbinil sorbinil: aldose reductase inhibitor. sorbinil : An azaspiro compound having a monofluoro-substituted chromane skeleton spiro-linked to an imidazolidinedione ring.	2	1	azaspiro compound; chromanes; imidazolidinone; organofluorine compound; oxaspiro compound	antioxidant; EC 1.1.1.21 (aldehyde reductase) inhibitor
imidazolidines [no description available]	2	1	azacycloalkane; imidazolidines; saturated organic heteromonocyclic parent
naphthoquinones Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.	2.7	3
5-(ethylsulfonyl)-2-(naphthalen-2-yl)benzo(d)oxazole ezutromid: a utrophin upregulator; structure in first source	2.25	1
salicylates Salicylates: The salts or esters of salicylic acids, or salicylate esters of an organic acid. Some of these have analgesic, antipyretic, and anti-inflammatory activities by inhibiting prostaglandin synthesis.. hydroxybenzoate : Any benzoate derivative carrying a single carboxylate group and at least one hydroxy substituent.. salicylates : Any salt or ester arising from reaction of the carboxy group of salicylic acid, or any ester resulting from the condensation of the phenolic hydroxy group of salicylic acid with an organic acid.. salicylate : A monohydroxybenzoate that is the conjugate base of salicylic acid.	2.05	1	monohydroxybenzoate	plant metabolite
hydroxymuconic semialdehyde (2Z,4E)-2-hydroxy-6-oxohexa-2,4-dienoic acid : A 2-hydroxy-6-oxohexa-2,4-dienoic acid in which the double bonds at positions 2 and 4 have Z- and E-configuration respectively.. 2-hydroxy-6-oxohexa-2,4-dienoic acid : A muconic semialdehyde having a hydroxy substituent at the 2-position.	2.05	1
dinitrobenzenes Dinitrobenzenes: Benzene derivatives which are substituted with two nitro groups in the ortho, meta or para positions.	1.99	1

Condition	Relationship Strength	Studies
Becker Muscular Dystrophy [description not available]	2.25	1
Muscular Dystrophy, Duchenne An X-linked recessive muscle disease caused by an inability to synthesize DYSTROPHIN, which is involved with maintaining the integrity of the sarcolemma. Muscle fibers undergo a process that features degeneration and regeneration. Clinical manifestations include proximal weakness in the first few years of life, pseudohypertrophy, cardiomyopathy (see MYOCARDIAL DISEASES), and an increased incidence of impaired mentation. Becker muscular dystrophy is a closely related condition featuring a later onset of disease (usually adolescence) and a slowly progressive course. (Adams et al., Principles of Neurology, 6th ed, p1415)	2.25	1
Disease Exacerbation [description not available]	1.99	1
Cataract, Membranous [description not available]	2.69	3
Cataract Partial or complete opacity on or in the lens or capsule of one or both eyes, impairing vision or causing blindness. The many kinds of cataract are classified by their morphology (size, shape, location) or etiology (cause and time of occurrence). (Dorland, 27th ed)	2.69	3
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2	1

1,2-dihydroxy-1,2-dihydronaphthalene

Description

Cross-References

Synonyms (19)

Research Excerpts

Bioavailability

Roles (2)

Drug Classes (2)

Research

Studies (13)

Market Indicators

Research Demand Index: 11.89

Study Types