147514-22-5

Basic information

• Product Name: 1,2-di-O-dodecyl-3-O-(glucopyranosyl)glycerol
• Synonyms: 1,2-di-O-dodecyl-3-O-(glucopyranosyl)glycerol
• CAS NO: 147514-22-5
• Molecular Formula: C33H62 O10
• Molecular Weight: 618.84
• Mol File: 147514-22-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 724.6°Cat760mmHg
• Flash Point: 215.4°C
• Appearance: /
• Density: 1.1g/cm³
• Vapor Pressure: 3.03E-24mmHg at 25°C
• Refractive Index: 1.505
• PKA: 12.88±0.70(Predicted)
• CAS DataBase Reference: 1,2-di-O-dodecyl-3-O-(glucopyranosyl)glycerol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-di-O-dodecyl-3-O-(glucopyranosyl)glycerol(147514-22-5)
• EPA Substance Registry System: 1,2-di-O-dodecyl-3-O-(glucopyranosyl)glycerol(147514-22-5)

Safety Data

• Hazardous Substances Data: 147514-22-5(Hazardous Substances Data)

Usage

Type of compound

Synthetic surfactant and emulsifying agent

Industries used in

Cosmetics and pharmaceuticals

Source

Derived from natural sources

Production method

Reaction of dodecyl alcohol with glycerol in the presence of acid catalysts, followed by the addition of glucose

Solubility

Excellent in both water and oil

Function

Effective emulsifier and stabilizer in formulations

Additional properties

Skin conditioning and moisturizing

Environmental concerns

Potential issues associated with production and use

Safety protocols

Proper environmental and safety protocols should be followed when handling it.

InChI:InChI=1/C33H62O10/c1-3-5-7-9-11-13-15-17-19-21-28(35)40-24-26(25-41-33-32(39)31(38)30(37)27(23-34)43-33)42-29(36)22-20-18-16-14-12-10-8-6-4-2/h26-27,30-34,37-39H,3-25H2,1-2H3/t26?,27-,30-,31+,32-,33-/m1/s1

Upstream product

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• 34382-09-7 <(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>methyl tetra-O-acetyl-β-D-glucopyranoside 
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• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 604-69-3 β-D-glucose pentaacetate 
• 58438-08-7 (2R)-1,2-di-O-benzyl-3-O-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosyl)glycerol 
• 74808-10-9 O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate 
• 55955-33-4 (2R)-1,2-di-O-benzyl-3-O-(2′,3′,4′,6′-tetra-O-acetyl-β-D-galactopyranosyl)glycerol 
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• 28069-18-3 1-(1’-β-D-[2’,3’,4’,6’-tetracetyl]galactosyl)glycerol 
• 4163-60-4 β-D-galactose peracetate 

Relevant articles and documents

Synthesis of dihydrosterculic acid-based monoglucosyl diacylglycerol and its analogues and their biological evaluation

In the present study, Lactobacillus plantarum glycolipid (GL1) molecule in β-configuration and its fatty acid analogues were synthesized using trichloroacetimidate methodology. The β-configuration of the GL1 molecule was unambiguously assigned by NMR studies using 2D-ROESY (NOE) and J-coupling analysis. Dihydrosterculic acid was synthesized using Furukawa's reagent and the selective esterification of dihydrosterculic acid at C-3 position of glycerol was achieved with EDC-HCl at 0 °C. In vitro cytotoxicity of the GL1 molecule and its fatty acid analogues was evaluated against DU145, A549, SKOV3 and MCF7 cell lines. Among all the synthesized molecules, the GL1 molecule and compound 7d showed moderate activity, while the compound 7b showed promising activity against all the tested cell lines with IC50 values of 20.1, 18.2, 19.1 and 17.6 ?1/4M, respectively. In addition, all tested compounds showed poor cytotoxicity against normal HUVEC cells. The MCF7 cells when treated with compound 7b showed lower bromodeoxyuridine incorporation levels as compared to untreated cells, suggesting that the compound 7b was highly effective and inhibited the cell proliferation. In addition, the compounds showed significant increase in caspases 3 and 9 levels by inducing apoptosis in MCF 7 cells.

Chemoenzymatic synthesis and antimicrobial activity evaluation of monogalactosyl diglycerides

Monogalactosyl diglycerides with medium to long fatty acid acyl chains, were prepared and examined for antimicrobial activity against Gram positive, Gram negative bacteria and fungi. The study of their in vitro antimicrobial activity confirms the significant activity of some monogalactosyl diacylglycerol analogues and establishes for the galactose series that the 1,2-disubstitution and the octanoyl chain are the proper structural features for the maximum activity.

Chemoenzymatic synthesis and antimicrobial activity evaluation of monoglucosyl diglycerides

Monoglucosyl diglycerides with medium-long length fatty acid acyl chains were prepared and examined for antimicrobial activity against Gram-positive, Gram-negative bacteria and fungi. The study of their in vitro antimicrobial activity confirms the significant activity of some monoglucosyl diacylglycerol analogues and establishes for the glucose series that the 1,2-disubstitution and the octanoyl chain are the proper structural features for the maximum activity.