35354-29-1

Basic information

• Product Name: 3,5-DIACETOXYBENZOIC ACID
• Synonyms: 3,5-DIACETOXYBENZOIC ACID;3,5-Diacethoxybenzoicacid;3,5-Bis(acetyloxy)benzoic acid
• CAS NO: 35354-29-1
• Molecular Formula: C₁₁H₁₀O₆
• Molecular Weight: 238.19
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Organic acids;Building Blocks for Dendrimers;Functional Materials
• Mol File: 35354-29-1.mol

Chemical Properties

• Melting Point: 158-160°C
• Boiling Point: 408.4 °C at 760 mmHg
• Flash Point: 160.408 °C
• Appearance: /
• Density: 1.344 g/cm³
• Vapor Pressure: 2.1E-07mmHg at 25°C
• Refractive Index: 1.543
• BRN: 2741728
• CAS DataBase Reference: 3,5-DIACETOXYBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DIACETOXYBENZOIC ACID(35354-29-1)
• EPA Substance Registry System: 3,5-DIACETOXYBENZOIC ACID(35354-29-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-60-37
• Hazardous Substances Data: 35354-29-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,5-DIACETOXYBENZOIC ACID is used as an intermediate in the synthesis of various pharmaceuticals for its anti-inflammatory properties and potential in developing new drugs for the treatment of cancer and diabetes.
Used in Agrochemical Industry:
3,5-DIACETOXYBENZOIC ACID is used as an intermediate in the production of agrochemicals, contributing to the development of effective and safe agricultural products.
Used in Organic Chemistry:
3,5-DIACETOXYBENZOIC ACID is used as a building block in the preparation of esters and amides, as well as in the synthesis of natural products and organic compounds, showcasing its versatility in organic chemistry.
Overall, 3,5-DIACETOXYBENZOIC ACID is a valuable chemical with diverse applications across different industries, particularly in pharmaceutical and agrochemical development, and as a key component in organic chemistry.

InChI:InChI=1/C11H10O6/c1-6(12)16-9-3-8(11(14)15)4-10(5-9)17-7(2)13/h3-5H,1-2H3,(H,14,15)

Upstream product

• 99-10-5 3,5-Dihydroxybenzoic acid 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 861446-17-5 3,5-bis(methoxymethoxy)benzoic chloride 

Downstream Products

• 39192-49-9 3,5-diacetoxybenzoyl chloride 
• 35354-30-4 3,5-diacetoxy-benzyl alcohol 
• 176378-93-1 acetic acid 3-acetoxy-5-(3-methyl-6-methylamino-2,4-dioxo-1-phenyl-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl)-phenyl ester 
• 176378-95-3 acetic acid 3-acetoxy-5-[6-dimethylamino-1-(4-fluoro-phenyl)-3-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl]-phenyl ester 
• 593249-77-5 C₁₆H₁₈O₇ 
• 905584-27-2 4-(3,5-diacetoxybenzoyloxy)benzaldehyde 
• 905584-43-2 3,5-diacetoxy-benzoic acid 4-[bis-(4-hydroxy-2-oxo-2H-chromen-3-yl)-methyl]-phenyl ester 
• 861446-27-7 (E)-3,5-diacetoxy-4'-fluorostilbene 
• 861446-19-7 3,5-diacetoxy-4'-chloroacetoxystilbene 
• 411233-14-2 4-hydroxy-3′,5′-diacetyl-trans-stilbene 
• 875544-28-8 3,5-diacetoxy-benzoic acid 2-phenylselanyl-ethyl ester 
• 3147-62-4 3,5-dihydroxybenzamide 
• 61227-18-7 3,5-diacetoxybenzamide 

Relevant articles and documents

Polyhydroxybenzoic acid derivatives as potential new antimalarial agents

With more than 200 million cases and 400,000 related deaths, malaria remains one of the deadliest infectious diseases of 2021. Unfortunately, despite the availability of efficient treatments, we have observed an increase in people infected with malaria since 2015 (from 211 million in 2015 to 229 million in 2019). This trend could partially be due to the development of resistance to all the current drugs. Therefore, there is an urgent need for new alternatives. We have, thus, selected common natural scaffolds, polyhydroxybenzoic acids, and synthesized a library of derivatives to better understand the structure–activity relationships explaining their antiplasmodial effect. Only gallic acid derivatives showed a noticeable potential for further developments. Indeed, they showed a selective inhibitory effect on Plasmodium (IC50 ~20 μM, SI > 5) often associated with interesting water solubility. Moreover, this has confirmed the critical importance of free phenolic functions (pyrogallol moiety) for the antimalarial effect. Methyl 4-benzoxy-3,5-dihydroxybenzoate (39) has, for the first time, been recognized as a potential lead for future research because of its marked inhibitory activity against Plasmodium falciparum and its significant hydrosolubility (3.72 mM).

Structure-activity relationship study and biological evaluation of SAC-Garlic acid conjugates as novel anti-inflammatory agents

A series of S-allyl-L-cysteine (SAC) with garlic acid conjugates as anti-inflammatory agents were designed and synthesized. Among the 40 tested compounds, SMU-8c exhibited the most potent inhibitory activity to Pam3CSK4-induced nitric oxide (NO) in RAW264.7 macrophages with IC50 of 22.54 ± 2.60 μM. The structure-activity relationship (SAR) study suggested that the esterified carboxyl group, carbon chain extension and methoxylation phenol hydroxy could improve the anti-inflammatory efficacy. Preliminary anti-inflammatory mechanism studies showed that SMU-8c significantly down-regulated the levels of Pam3CSK4 triggered TNF-α cytokine in human THP-1 cells, mouse RAW 264.7 macrophages, as well as in ex-vivo human peripheral blood mononuclear cells (PBMC) with no influence on cell viability. SMU-8c specifically blocked the Pam3CSK4 ignited secreted embryonic alkaline phosphatase (SEAP) signaling with no influence to Poly I:C or LPS triggered TLR3 or TLR4 signaling. Moreover, SMU-8c suppressed TLR2 in HEK-Blue hTLR2 cells and inhibited the formation of TLR1-TLR2, and TLR2-TLR6 complex in human PBMC. In summary, SMU-8c inhibited the TLR2 signaling pathway to down-regulate the inflammation cytokines, such as NO, SEAP and TNF-α, to realize its anti-inflammatory activity.

Preparation method of 3,5-dihydroxybenzyl alcohol

The invention relates to a preparation method of a medical and chemical intermediate 3,5-dihydroxybenzyl alcohol. The method comprises the following steps of: with commercially available 3,5-dihydroxy-benzoic acid as a raw material, preparing 3,5-diacetoxybenzoic acid through an acetylation reaction; reducing carboxyl into alcohol by a sodium borohydride/iodine borohydride system; and finally, performing acetyl de-protection using a weak base solution to obtain the target product 3,5-dihydroxybenzyl alcohol. The synthesis path has the characteristics of cheap and easily available reagent, mild reaction conditions, easiness in operation, easiness in product separation, relatively high yield and the like.

The application of template selectophores for the preparation of molecularly imprinted polymers

Molecularly imprinted polymers are versatile materials with wide application scope for the detection, capture and separation of specific compounds present in complex feed stocks. A major challenge associated with their preparation has been the need to sacrifice one mole equivalent of the template molecule to generate the complementary polymer cavities that selectively bind the target molecule. Moreover, template molecules can often be difficult to synthesise, expensive or lack stability. In this study, we describe a new approach, directed at the use of synthetic selectophores, chosen as readily prepared and low cost structural analogues with recognition groups in similar three-dimensional arrangements as found in the target molecule. To validate the approach, a comparative study of selectophores related to the polyphenolic compound (E)-resveratrol has been undertaken using traditional and green chemical synthetic approaches. These molecular mimic compounds were employed as polymer templates and also as binding analytes to interrogate the recognition sites associated with the molecularly imprinted polymers. Importantly, the study confirms that the use of selectophores has the potential to confer practical advantages, including access to more efficient methods for selection and preparation of suitable template molecules with a broader range of molecular diversity, as well as delivering imprinted polymers capable of recognizing the target compound and structurally related products.

Bimolecular catalysis and turnover from a macromolecular host system

The synthesis of a globular macromolecule and its application as a bimolecular catalyst are reported. The macromolecular structure supports (at least) two zinc-metalated porphyrin units, each capable of binding a single reactant. The proximity of the two

MOLECULARLY IMPRINTED POLYMERS

The present invention provides methods of designing molecularly imprinted polymers (MIPs) which have applications in extracting bioactive compounds from a range of bioprocessing feedstocks and wastes. The present invention is further directed to MIPs designed by the methods of the present invention.

PREPARATION METHOD OF ACYLBENZENES

A process for the production of acylbenzenes, comprising reacting diacetoxybenzoyl chloride with a Grignard reagent in the presence of an iron-containing catalyst. The acylbenzenes are useful intermediates in a multistep process for the preparation of resveratrol.

PREPARATION METHOD OF ACYLBENZENES

A process for the production of acylbenzenes, comprising reacting diacetoxybenzoyl chloride with a Grignard reagent in the presence of an iron-containing catalyst. The acylbenzenes are useful intermediates in a multistep process for the preparation of resveratrol.

Studies on depigmenting activities of dihydroxyl benzamide derivatives containing adamantane moiety

Six diphenolic compounds containing adamantane moiety were synthesized and evaluated as potent inhibitors on tyrosinase activity and melanin formation in melan-a cells. The inhibitory activity of 4-adamantyl resorcinol 1 was similar to that of 4-n-butyl resorcinol in both assays. However, dihydroxyl benzamide derivatives 6a-e showed different inhibitory patterns. All derivatives significantly suppressed the cellular melanin formation without tyrosinase inhibitory activities. These behaviors indicated that the introduction of amide bond changes the binding mode of dihydroxyl groups to tyrosinase. Among derivatives, 6d (3,4-dihydroxyl compound) and 6e (2,3-dihydroxyl compound) showed stronger inhibitory activities (IC50 = 1.25 μM and 0.73 μM, respectively) as compared to 4-n-butyl resorcinol (IC50 = 21.64 μM) and hydroquinone (IC50 = 3.97 μM). This study showed that the position of dihydroxyl substituent at aromatic ring is important for the intercellular inhibition of melanin formation, and also amide linkage and adamantane moiety enhance the inhibition.

Novel Sirtuin Activating Compounds and Methods for Making the Same

The present invention includes methods for preparing resveratrol, resveratrol esters and substituted and unsubstituted stilbenes of the formula given below; where each Y is —O or halogen, each Z is —O or halogen, each n and each m is independently the value of 0, 1, 2, 3, 4 or 5, each A and each B is independently selected from Pn, R or absent, each V and each W is independently selected from Pn, straight or branched alkyl of from (2) to (6) carbon atoms and cycloalkyl of from (3) to (8) carbon atoms, alkoxy, phenyl, benzyl or halogen, R is independently selected from the group comprising alkyl with at least one carbon atom, aryl and aralkyl, Pn is an alcohol protecting group and diastereoisomers of the foregoing. The compounds are made from a multi-step process including a N-heterocyclic carbon-type ligand coupling in the presence of a base with benzyol halide and styrene coupling partners. These compounds show increased stability for use in the food, cosmetic and pharmaceutical industries.