99-10-5

Basic information

• Product Name: 3,5-Dihydroxybenzoic acid
• Synonyms: 3,5-dihydroxy-benzoicaci;5-carboxyresorcinol;Benzoicacid,3,5-dihydroxy-;DOHBA;A-RESORCYLIC ACID;3,5-DIHYDROXYBENZOIC ACID;ALPHA-RESERCYLIC ACID;ALPHA-RESORCYLIC ACID
• CAS NO: 99-10-5
• Molecular Formula: C₇H₆O₄
• Molecular Weight: 154.12
• EINECS: 202-730-7
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic acid;Organic acids;Building Blocks for Dendrimers;Functional Materials;Building Blocks;C7;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks;Aromatics, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 99-10-5.mol

Chemical Properties

• Melting Point: 236-238 °C (dec.)(lit.)
• Boiling Point: 237.46°C (rough estimate)
• Flash Point: 200 °C
• Appearance: Off-white to beige/Powder
• Density: 1.3725 (rough estimate)
• Vapor Pressure: 1.64E-07mmHg at 25°C
• Refractive Index: 1.6400 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: Soluble in 50 mg/mL, 95% Ethanol.
• PKA: 4.04(at 25℃)
• Water Solubility: 84 g/L (20 ºC)
• BRN: 2207864
• CAS DataBase Reference: 3,5-Dihydroxybenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Dihydroxybenzoic acid(99-10-5)
• EPA Substance Registry System: 3,5-Dihydroxybenzoic acid(99-10-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 1
• RTECS: VH3708000
• TSCA: Yes
• Hazardous Substances Data: 99-10-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3,5-Dihydroxybenzoic acid is used as an intermediate in organic synthesis for the production of various pharmaceutical compounds and other organic molecules.
Used in Pharmaceutical Industry:
3,5-Dihydroxybenzoic acid is used as an intermediate for the development of pharmaceuticals, contributing to the synthesis of drugs with potential therapeutic applications.
Used as a Biomarker:
3,5-Dihydroxybenzoic acid serves as a biomarker for whole grain wheat and rye, indicating the presence and consumption of these dietary components. This can be useful in nutritional studies and assessing the health benefits of whole grains.

InChI:InChI=1/C7H6O4/c8-5-1-4(7(10)11)2-6(9)3-5/h1-3,8-9H,(H,10,11)/p-1

Synthetic route

3,5-dimethoxybenzoic acid (1132-21-4) → 3,5-Dihydroxybenzoic acid (99-10-5)

Conditions	Yield
With Cyclohexyl iodide In N,N-dimethyl-formamide for 3h; Heating;	92%

(E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol (501-36-0) → 3,5-Dihydroxybenzoic acid (99-10-5) + 4-hydroxy-benzaldehyde (123-08-0)

Conditions	Yield
With dihydrogen peroxide In water; acetone at 40℃; for 1h; Reagent/catalyst;	A 46% B 73%

3,5-dibromobenzoic acid (618-58-6) → 3,5-Dihydroxybenzoic acid (99-10-5)

Conditions	Yield
With calcium hydroxide; water; copper at 160 - 170℃;

3,6-dichlorophthalic acid (16110-99-9) → 3,5-Dihydroxybenzoic acid (99-10-5)

Conditions	Yield
With copper at 310℃; bei der Kalischmelze;

Upstream product

• 618-58-6 3,5-dibromobenzoic acid 
• 16110-99-9 3,6-dichlorophthalic acid 
• 121-48-2 3,5-disulfonicbenzoic acid 
• 65-85-0 benzoic acid 
• 82850-46-2 Leprocybosid 
• 6486-61-9 1,2,7-trihydroxy-chromeno[5,4,3-cde]chromene-5,10-dione 
• 68218-49-5 3,4,6-triiodo-phthalic acid-anhydride 
• 7732-18-5 water 
• 3324-76-3 β-tropolone 
• 33716-83-5 (2,4-dimethoxy-6-methyl-phenyl)-(3-methoxy-5-methyl-phenyl)-ether 
• 10034-85-2 hydrogen iodide 
• 46329-68-4 3-hydroxy-5-sulfo-benzoic acid 
• 11029-16-6 2-(3,5-dichloro-2,6-dihydroxy-4-methylbenzoyl)-5-hydroxy-3-methoxybenzoic acid 
• 82850-45-1 Leprocybin 

Downstream Products

• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 
• 37622-58-5 3,5-dihydroxy-benzoic acid propyl ester 
• 4142-98-7 ethyl 3,5-dihydroxybenzoate 
• 37622-60-9 pentyl 3,5-dihydroxybenzoate 
• 37622-62-1 3,5-dihydroxy-benzoic acid heptyl ester 
• 61169-36-6 1,2,4,5,6,8-hexahydroxy-9,10-anthraquinone 
• 16534-12-6 3,5-dihydroxy-4-bromobenzoic acid 
• 33580-60-8 2,3,5-trihydroxybenzoic acid 
• 87251-21-6 2-chloro-3,5-dihydroxy-benzoic acid 
• 42858-60-6 3,5-cyclohexanedione-1-carboxylic acid 
• 6486-61-9 1,2,7-trihydroxy-chromeno[5,4,3-cde]chromene-5,10-dione 
• 82361-26-0 hexachloro-4-cyclohexene-1,3-dione 
• 122650-23-1 18-(3,5-bis-ethoxycarbonyloxy-benzoyloxy)-11,17-dimethoxy-yohimbane-16-carboxylic acid methyl ester 
• 108-46-3 recorcinol 

Relevant articles and documents

A chlorogenic acid esterase from a metagenomic library with unique substrate specificity and its application in caffeic and ferulic acid production from agricultural byproducts

Soil microbes are an abundant source of enzymes with unique properties that may be useful for industrial applications. As most wild-type strains show low chlorogenic acid esterase expression and activity, and most microbes cannot be cultured in the laboratory, a metagenomic approach provides methods of identifying new enzymes. In this study, a gene encoding a chlorogenic acid esterase, named Tan410, was isolated from a soil metagenomic library and overexpressed in Escherichia coli BL21 (DE3). The recombinant enzyme, with a predicted molecular weight of 54.88 kDa, was purified to homogeneity. The K m and V max values for Tan410 were 1.26 mM and 0.33 mM min–1, respectively, with chlorogenic acid as the substrate. Its optimum temperature and pH for reaction were 30 °C and 7.5, respectively. The enzyme exhibited moderate thermostability and broad pH stability (3.0–10.0). Tan410 was also able to hydrolyse ethyl ferulate, methyl caffeate, propyl gallate, ethyl gallate, methyl vanillate, methyl benzoate, ethyl benzoate, methyl 2,5-dihydroxybenzoate, and methyl 3,5-dihydroxybenzoate, and it released caffeic and ferulic acids from agricultural byproducts (destarched wheat bran and coffee pulp). Tan140 has potential for industrial application in biomass valorization.

The comparison of the photocatalytic performance shown by TiO2 and TiO2/WO3 composites—a parametric and kinetic study

Kinetic and mechanistic related approaches for mostly titania were intensively studied in the literature. However, combined modelling and kinetic studies are few. Therefore, the present work focuses on modelling the dependence of the degradation kinetics of two model compounds (salicylic acid—SA and methyl orange—MO) on Evonik Aeroxide P25, hydrothermally prepared hierarchical TiO2 and P25/WO3 nanostars, obtained also by hydrothermal crystallization. The obtained individual semiconductors and the composites were characterized using XRD, DRS, SEM, while the photocatalytic degradation of the model pollutants were carried out varying the catalyst load, the initial pollutant concentration and incident light intensity. It was found that the degradation kinetics were independent from the hierarchical nature of the material, while significant dependencies of the degradation efficiency was found from the previously mentioned investigation parameters. All these parametric interdependences were successfully studied and a kinetic model was proposed for both bare TiO2 and TiO2/WO3 composite systems.

Synthesis method of 3,5-dimethoxybenzoic acid ethyl ester

The invention discloses a synthesis method of 3,5-dimethoxybenzoic acid ethyl ester, and belongs to the field of chemosynthesis. According to the method, benzene is firstly used for producing resorcinol under specific conditions; under the condition of using dimethylformamide as a solvent by anhydrous potassium carbonate and carbon dioxide, the 3,5-dihydroxy-benzoic acid is finally obtained through impurity removal, decoloring, pH value regulation and cooling crystallization; then, the 3,5-dihydroxy-benzoic acid is mixed with dimethyl sulfate in a stirring condition; a sodium hydroxide solution is dropwise added into the materials for backflow; the pH value is regulated after the backflow; the pressure reduction filtering, washing and drying are carried out after cooling to 0 DEG C; the 3,5-dimethoxybenzoic acid is obtained; finally, the 3,5-dimethoxybenzoic acid is esterified with absolute ethyl alcohol under the condition of concentrated sulfuric acid; finally, the 3,5-dimethoxybenzoic acid ethyl ester is obtained.

Inclusion complex containing epoxy resin composition for semiconductor encapsulation

The invention is an epoxy resin composition for sealing a semiconductor, including (A) an epoxy resin and (B) a clathrate complex. The clathrate complex is one of (b1) an aromatic carboxylic acid compound, and (b2) at least one imidazole compound represented by formula (II): wherein R2 represents a hydrogen atom, C1-C10 alkyl group, phenyl group, benzyl group or cyanoethyl group, and R3 to R5 represent a hydrogen atom, nitro group, halogen atom, C1-C20 alkyl group, phenyl group, benzyl group, hydroxymethyl group or C1-C20 acyl group. The composition has improved storage stability, retains flowability when sealing, and achieves an effective curing rate applicable for sealing delicate semiconductors.

Metal incorporated Horseradish Peroxidase (HRP) catalyzed oxidation of resveratrol: Selective dimerization or decomposition

Horseradish Peroxidase (HRP) is a commercially available and prevalently used peroxidase with no specific substrate binding domain. However, after being incorporated with different metal cations, new catalytic functions were found in biomimetic oxidation of resveratrol. Based on the results of screening, Ca, Cu, Fe and Mn incorporated enzymes showed distinctive effects, either decomposition or dimerization products were observed.

Radical-induced oxidation of trans-resveratrol

trans-Resveratrol (RVT) (3,5,4′-trihydroxystilbene), a polyphenolic constituent of red wine, is thought to be beneficial in reducing the incidence of cardiovascular diseases, partly via its antioxidant properties. However, the mechanism of action by which trans-resveratrol displays its antioxidant effect has not been totally unravelled. This study aimed at establishing a comprehensive scheme of the reaction mechanisms of the direct scavenging of HO and O2- radicals generated by water gamma radiolysis. Aerated aqueous solutions of trans-RVT (from 10 to 100 μmol L-1) were irradiated with increasing radiation doses (from 25 to 400 Gy) and further analyzed by UV-visible absorption spectrophotometry for detection of trans-RVT oxidation products. Separation and quantification of RVT and its four oxidation products previously identified by mass spectrometry, i.e., piceatannol (PCT), 3,5-dihydroxybenzoic acid (3,5-DHBA), 3,5-dihydroxybenzaldehyde (3,5-DHB) and para-hydroxybenzaldehyde (PHB), were performed by HPLC/UV-visible spectrophotometry. Determination of the radiolytic yields of trans-RVT consumption and oxidation product formation has allowed us to establish balance between trans-RVT disappearance and the sum of oxidation products formation. Under our conditions, O2- radicals seemed to poorly initiate oxidation of trans-RVT, whereas the latter, whatever its initial concentration, quantitatively reacted with HO radicals, via a dismutation mechanism. Two reaction pathways involving HO-induced trans-RVT primary radicals have been proposed to explain the formation of the oxidation end-products of trans-RVT.

PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS

The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.

Liquid chromatographic/electrospray ionization mass spectrometric identification of the oxidation end-products of trans-resveratrol in aqueous solutions

trans-Resveratrol (3,5,4′-trihydroxystilbene) is a natural polyphenolic compound that exhibits antioxidant properties. Our study aimed at studying the HO*-induced oxidation of resveratrol (100 μmol.L-1) in aerated aqueous solutions. Gamma radiolysis of water was used to generate HO*/O2- free radicals (I=10 Gy.min-1, dose=400 Gy). Oxidation products were identified by direct infusion mass spectrometry and high-performance liquid chromatography/mass spectrometry. For each product, structural elucidation was based on simple mass spectra, fragmentation spectra and deuterium/hydrogen exchange spectra; the comparison with mass spectra of synthetic products provided valuable information allowing the complete identification of the oxidation products. Four products resulting from the direct attack of HO. radicals towards resveratrol were identified respectively as piceatannol (trans-3,5,3′,4′-tetrahydroxystilbene), 3,5-dihydroxybenzoic acid, 3,5-dihydroxybenzaldehyde and 4-hydroxybenzaldehyde.

A [2+3] fragment coupling approach to N,O-bridged calix[1]arene[4]pyridines and their complexation with C60

Functionalized N,O-bridged calix[1]arene[4]pyridines, first examples of the odd-numbered heterocalixaromatics containing mixed heteroatom bridges and mixed aromatic units, have been synthesized from the Pd2(dba)3/dppp-catalyzed 2+3 m

An efficient method for demethylation of aryl methyl ethers

A new efficient method for demethylation of aryl methyl ethers using iodocyclohexane in DMF under reflux condition is described.