86404-07-1

Basic information

• Product Name: O³-benzyl-O⁵,O⁶-(1-methylethylidene)-L-ascorbic acid
• Synonyms: O³-benzyl-O⁵,O⁶-(1-methylethylidene)-L-ascorbic acid
• CAS NO: 86404-07-1
• Molecular Weight: 306.315
• Mol File: 86404-07-1.mol
• Article Data: 24

Chemical Properties

• CAS DataBase Reference: O³-benzyl-O⁵,O⁶-(1-methylethylidene)-L-ascorbic acid(CAS DataBase Reference)
• NIST Chemistry Reference: O³-benzyl-O⁵,O⁶-(1-methylethylidene)-L-ascorbic acid(86404-07-1)
• EPA Substance Registry System: O³-benzyl-O⁵,O⁶-(1-methylethylidene)-L-ascorbic acid(86404-07-1)

Safety Data

• Hazardous Substances Data: 86404-07-1(Hazardous Substances Data)

Upstream product

• 50271-42-6 5,6-O-isopropylidene-D-isoascorbic acid 
• 100-39-0 benzyl bromide 
• 89-65-6 isoascorbic acid 
• 15042-01-0 5,6-O-isopropylidene-L-ascorbic acid 
• 2871-84-3 (R)-3,4-bis(benzyloxy)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)furan-2(5H)-one 
• 50-81-7 ascorbic acid 
• 100-44-7 benzyl chloride 
• 146-75-8 sodium L-ascorbate 
• 67-64-1 acetone 

Downstream Products

• 86404-08-2 (2R)-3-benzyloxy-2-[(1S)-1,2-dihydroxyethyl]-4-hydroxy-2H-furan-5-one 
• 562043-84-9 2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-O-benzyl-5,6-O-isopropylidene-L-ascorbic acid 

Relevant articles and documents

Chemistry of L-ascorbic acid. IV. Regioselective O-alkylation of 5,6-O-isopropylidene-L-ascorbic acid using CsF

The regioselective 3-O-alkylation of 5,6-O-isopropylidene-L-ascorbic acid is achieved under mild conditions using CsF as a base.

Synthesis and Biological Evaluation of Ascorbyl-Conjugated Peptide Derivatives as Collagen Synthesis Stimulating Agents in Human Skin Fibroblasts

Vitamin C (ascorbic acid) is a widely used agent for anti-aging and whitening in the field of cosmetics. It affects collagen production in skin cells, inhibits melanin synthesis, displays anti-oxidant activity, and improves the immune system. However, vitamin C has limitations in cell permeability and environmental condition such as heating and lighting decrease its stability. Thus, vitamin C derivatives are being developed to overcome these problems. In this study, we synthesized vitamin C derivatives with a succinoyl group at the 2-position and peptides in the form of ester bonds. We then evaluated the cytotoxicity and collagen synthesis activity of these new compounds in human skin fibroblasts. Vitamin C-conjugated peptides were also synthesized in ether and carbamate forms, and the optimal combination conditions of vitamin C and peptides were identified. In addition, collagen synthesis-stimulating activity of vitamin C-conjugated peptides was also evaluated and compared to the effects of vitamin C alone. Based on these results, we confirmed that the ester-bonded vitamin C-conjugated peptide GEKG showed more stimulating effect on the production of collagen and related gene expression than either vitamin C or GEKG alone. This study will provide important information for developing skin health products and other topical cosmetics using vitamin C and peptides.

Discovery of a stable vitamin C glycoside in crab apples (Malus sylvestris)

Non-targeted LC-MS metabolomics on fruit of three wild and domesticated apple species (Malus sylvestris, M. sieversii and M. domestica) showed that two crab apple (M. sylvestris) accessions were distinguished by high concentrations of an ascorbic acid glycoside (AAG). This was partly purified, but key NMR signals were masked by inseparable sucrose. Reference samples of 2-O-β-D-glucopyranosyl L-ascorbic acid and 2-O-β-D-galactopyranosyl L-ascorbic acid were synthesised, but both coincided with the crab apple AAG on LC-MS. Peracetylation of the crab apple extract allowed both purification and characterisation, and the AAG was proven to be 2-O-β-D-glucopyranosyl L-ascorbic acid by comparison of 1H NMR, HRMS and HPLC data with synthesised peracetylated ascorbyl glycoside standards. The stability of the natural AA 2-β-glycoside was similar to synthetic 2-O-α-D-glucopyranosyl L-ascorbic acid, used widely in cosmetic and pharmaceutical products. This discovery in crab apples (Rosaceae) is only the fourth reported occurrence of any ascorbyl glycoside from plants, the others being from Cucurbitaceae, Solanaceae and Brassicaceae. It is hypothesised that AAGs may be more widespread in plants than currently realised.