90904-23-7

Basic information

• Product Name: 1,2-Propanediol, 3-(dodecyloxy)-, (R)-
• Synonyms: (-)-3-dodecyloxy-propane-1,2-diol;(-)-3-Dodecyloxy-propan-1,2-diol;(-)-O1-Dodecyl-glycerin;3-O-dodecyl-sn-glycerol;(R)-3-Dodecyloxy-propane-1,2-diol
• CAS NO: 90904-23-7
• Molecular Formula: C15H32O3
• Molecular Weight: 260.41300
• Mol File: 90904-23-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 390.5±22.0 °C(Predicted)
• Density: 0.937±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 1,2-Propanediol, 3-(dodecyloxy)-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Propanediol, 3-(dodecyloxy)-, (R)-(90904-23-7)
• EPA Substance Registry System: 1,2-Propanediol, 3-(dodecyloxy)-, (R)-(90904-23-7)

Safety Data

• Hazardous Substances Data: 90904-23-7(Hazardous Substances Data)

Usage

Description

1,2-Propanediol, 3-(dodecyloxy)-, (R)-, also known as 3-O-Dodecyl-sn-glycerol, is a chiral secondary alcohol with a dodecyloxy group attached to the third carbon. It is a versatile organic compound with potential applications in various industries.

Uses

Used in Pharmaceutical Industry:
1,2-Propanediol, 3-(dodecyloxy)-, (R)is used as a key intermediate in the synthesis of cysteine-based lipopeptides and compositions. These lipopeptides act as Toll-like receptor 2 (TLR2) agonists, which play a crucial role in modulating the immune response. They are useful for treating a wide range of conditions, including infections, inflammations, respiratory, dermatological, and autoimmune diseases.

Upstream product

• 51323-71-8 dodecyl mesylate 
• 22323-82-6 (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol 
• 478549-98-3 3-O-dodecyl-1,2-O-isopropylidene-sn-glycerol 
• 143-15-7 1-dodecylbromide 
• 112-53-8 1-dodecyl alcohol 
• 57044-25-4 (R)-oxiranemethanol 

Downstream Products

• 96022-95-6 2-O-Benzyl-3-O-dodecyl-sn-glycerin 
• 106881-92-9 C₄₁H₅₂O₃ 
• 96022-69-4 2-O-Benzyl-3-O-dodecyl-1-O-<2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranosyl>-sn-glycerin 
• 478550-18-4 3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2-deoxy-1-O-dodecyl-2-octadecanamido-sn-glycerol 
• 478550-15-1 3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2-deoxy-2-dodecanamido-1-O-dodecyl-sn-glycerol 
• 478550-11-7 2-azido-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2-deoxy-1-O-dodecyl-sn-glycerol 
• 478550-08-2 2-azido-2-deoxy-1-O-dodecyl-sn-glycerol 
• 96093-52-6 3-O-Dodecyl-1-O-trityl-sn-glycerin 

Relevant articles and documents

Autotaxin structure-activity relationships revealed through lysophosphatidylcholine analogs

Autotaxin (ATX) catalyzes the hydrolysis of lysophosphatidylcholine (LPC) to form the bioactive lipid lysophosphatidic acid (LPA). LPA stimulates cell proliferation, cell survival, and cell migration and is involved in obesity, rheumatoid arthritis, neuropathic pain, atherosclerosis and various cancers, suggesting that ATX inhibitors have broad therapeutic potential. Product feedback inhibition of ATX by LPA has stimulated structure-activity studies focused on LPA analogs. However, LPA displays mixed mode inhibition, indicating that it can bind to both the enzyme and the enzyme-substrate complex. This suggests that LPA may not interact solely with the catalytic site. In this report we have prepared LPC analogs to help map out substrate structure-activity relationships. The structural variances include length and unsaturation of the fatty tail, choline and polar linker presence, acyl versus ether linkage of the hydrocarbon chain, and methylene and nitrogen replacement of the choline oxygen. All LPC analogs were assayed in competition with the synthetic substrate, FS-3, to show the preference ATX has for each alteration. Choline presence and methylene replacement of the choline oxygen were detrimental to ATX recognition. These findings provide insights into the structure of the enzyme in the vicinity of the catalytic site as well as suggesting that ATX produces rate enhancement, at least in part, by substrate destabilization.

Stereoselective Synthesis of Long-chain 1-O-(β-D-Maltosyl)-3-O-alkyl-sn-glycerols (Alkyl Glyceryl Ether Lysoglycolipids)

The synthesis of long-chain 2-O-benzyl-3-O-alkyl-sn-glycerols 5 was improved, making these compounds easily accessible for glycosylation experiments.Glycosylation with α-acetobromomaltose following a modified Koenings-Knorr procedure after removal of the protective groups yielded the title compound 9 in good yields.These compounds represent examples of alkyl glyceryl ether lysoglycolipids.Some properties of these amphiphilic compounds with a nonionic carbohydrate head-group differ not much (critical micell concentration, hemolytic activity), other properties differ very much (antitumor efficiency) from the properties of the analogous compounds with a zwitterionic phosphorylcholine head-group.