6752-75-6

Basic information

• Product Name: (2-acetyloxy-4-methoxy-9-phenyl-5,8,10-trioxabicyclo[4.4.0]dec-3-yl) acetate
• CAS NO: 6752-75-6
• Molecular Formula: C₁₈H₂₂O₈
• Molecular Weight: 366.368
• Mol File: 6752-75-6.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 466.5°Cat760mmHg
• Flash Point: 204.2°C
• Density: 1.29g/cm³
• CAS DataBase Reference: (2-acetyloxy-4-methoxy-9-phenyl-5,8,10-trioxabicyclo[4.4.0]dec-3-yl) acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (2-acetyloxy-4-methoxy-9-phenyl-5,8,10-trioxabicyclo[4.4.0]dec-3-yl) acetate(6752-75-6)
• EPA Substance Registry System: (2-acetyloxy-4-methoxy-9-phenyl-5,8,10-trioxabicyclo[4.4.0]dec-3-yl) acetate(6752-75-6)

Safety Data

• Hazardous Substances Data: 6752-75-6(Hazardous Substances Data)

Usage

Description

(2-acetyloxy-4-methoxy-9-phenyl-5,8,10-trioxabicyclo[4.4.0]dec-3-yl) acetate, also known as salicin, is a natural chemical compound derived from the bark of the willow tree and other related plants. It is a white, crystalline substance with pain-relieving and anti-inflammatory properties, which is converted into salicylic acid in the body, the active ingredient in aspirin.
Used in Pharmaceutical Industry:
(2-acetyloxy-4-methoxy-9-phenyl-5,8,10-trioxabicyclo[4.4.0]dec-3-yl) acetate is used as a natural alternative to aspirin for its pain-relieving and anti-inflammatory properties, making it suitable for treating conditions such as pain, fever, and inflammation.
Used in Cosmetic and Skincare Industry:
(2-acetyloxy-4-methoxy-9-phenyl-5,8,10-trioxabicyclo[4.4.0]dec-3-yl) acetate is used as an ingredient in cosmetic and skincare products for its anti-inflammatory and analgesic properties, helping to soothe and reduce inflammation in the skin.
However, it is important to note that salicin can cause adverse reactions in some individuals, particularly those with allergies or sensitivities to aspirin, and should be used with caution.

Upstream product

• 110-86-1 pyridine 
• 108-24-7 acetic anhydride 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 75-36-5 acetyl chloride 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 100-52-7 benzaldehyde 
• 2774-23-4 methyl 2-O-acetyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 67-68-5 dimethyl sulfoxide 
• 4148-58-7 (4aR,6S,7S,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 26295-65-8 (4aR,6S,7S,8S,8aR)-7,8-Bis-(1-ethoxy-ethoxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 3162-96-7 methyl-4,6-O-phenylmethylene-α-D-mannopyranoside 
• 65530-27-0 (2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine 

Downstream Products

• 162284-50-6 methyl 2,3-di-O-acetyl-6-O-benzyl-α-D-glucopyranoside 
• 18929-80-1 methyl 2,3-di-O-acetyl-4-O-benzoyl-6-bromo-6-deoxy-α-D-glucopyranoside 
• 29868-43-7 methyl 2,3-di-O-acetyl-6-O-benzoyl-α-D-glucopyranoside 
• 56543-18-1 methyl 2,3-di-O-acetyl-4-O-benzoyl-α-D-glucopyranoside 
• 1384472-24-5 C₁₈H₂₄O₈ 
• 1214746-77-6 methyl 2,3-di-O-acetyl-4-O-benzoyl-α-D-mannopyranoside 
• 1214746-75-4 methyl 2,3-di-O-acetyl-6-O-benzoyl-α-D-mannopyranoside 
• 1128-40-1 methyl β-L-fucopyranoside 
• 73139-33-0 methyl-2,3-di-O-acetyl-4-O-benzoyl-6-desoxy-α-D-arabino-hex-5-enopyranoside 
• 205755-06-2 Succinic acid mono-{(2R,3R,4S,5R,6S)-4,5-diacetoxy-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-6-methoxy-tetrahydro-pyran-3-yl} ester 
• 477949-33-0 Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester 
• 604-70-6 Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yl ester 
• 7177-79-9 methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside 

Relevant articles and documents

In Situ Switching of Site-Selectivity with Light in the Acetylation of Sugars with Azopeptide Catalysts

We present a novel concept for the in situ control of site-selectivity of catalytic acetylations of partially protected sugars using light as external stimulus and oligopeptide catalysts equipped with an azobenzene moiety. The isomerizable azobenzene-peptide backbone defines the size and shape of the catalytic pocket, while the π-methyl-l-histidine (Pmh) moiety transfers the electrophile. Photoisomerization of the E- to the Z-azobenzene catalyst (monitored via NMR) with an LED (λ = 365 nm) drastically changes the chemical environment around the catalytically active Pmh moiety, so that the light-induced change in the catalyst shape alters site-selectivity. As a proof of principle, we employed (4,6-O-benzylidene)methyl-α-d-pyranosides, which provide a change in regioselectivity from 2:1 (E) to 1:5 (Z) for the monoacetylated products at room temperature. The validity of this new catalyst-design concept is further demonstrated with the regioselective acetylation of the natural product quercetin. In situ irradiation NMR spectroscopy was used to quantify photostationary states under continuous irradiation with UV light.

Diisopropylethylamine-triggered, highly efficient, self-catalyzed regioselective acylation of carbohydrates and diols

A diisopropylethylamine (DIPEA)-triggered, self-catalyzed, regioselective acylation of carbohydrates and diols is presented. The hydroxyl groups can be acylated by the corresponding anhydride in MeCN in the presence of a catalytic amount of DIPEA. This method is comparatively green and mild as it uses less organic base compared with other selective acylation methods. Mechanistic studies indicate that DIPEA reacts with the anhydride to form a carboxylate ion, and then the carboxylate ion could catalyze the selective acylation through a dual H-bonding interaction.

Benzylidene Acetal Protecting Group as Carboxylic Acid Surrogate: Synthesis of Functionalized Uronic Acids and Sugar Amino Acids

Direct oxidation of the 4,6-O-benzylidene acetal protecting group to C-6 carboxylic acid has been developed that provides an easy access to a wide range of biologically important and synthetically challenging uronic acid and sugar amino acid derivatives in good yields. The RuCl3-NaIO4-mediated oxidative cleavage method eliminates protection and deprotection steps and the reaction takes place under mild conditions. The dual role of the benzylidene acetal, as a protecting group and source of carboxylic acid, was exploited in the efficient synthesis of six-carbon sialic acid analogues and disaccharides bearing uronic acids, including glycosaminoglycan analogues.