6145-69-3

Basic information

• Product Name: 1-O-HEXADECYL-RAC-GLYCEROL
• Synonyms: 1-O-HEXADECYL-RAC-GLYCEROL;3-(HEXADECYLOXY)-1,2-PROPANEDIOL;DL-CHIMYL ALCOHOL;DL-ALPHA-HEXADECYLGLYCEROL;CHIMYL ALCOHOL;RAC-GLYCEROL-1-HEXADECYL ETHER;(±)-3-(hexadecyloxy)propane-1,2-diol;alpha-hexadecylglycerol
• CAS NO: 6145-69-3
• Molecular Formula: C₁₉H₄₀O₃
• Molecular Weight: 316.52
• EINECS: 228-149-9
• Mol File: 6145-69-3.mol
• Article Data: 25

Chemical Properties

• Melting Point: 60-65 °C
• Boiling Point: 445.2±25.0 °C(Predicted)
• Appearance: /
• Density: 0.920±0.06 g/cm3(Predicted)
• Storage Temp.: −20°C
• PKA: 13.68±0.20(Predicted)
• CAS DataBase Reference: 1-O-HEXADECYL-RAC-GLYCEROL(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O-HEXADECYL-RAC-GLYCEROL(6145-69-3)
• EPA Substance Registry System: 1-O-HEXADECYL-RAC-GLYCEROL(6145-69-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 6145-69-3(Hazardous Substances Data)

Usage

Uses

1-O-Hexadecyl-rac-glycerol is used in the synthesis of N-linked and diglycosylated glucosamine-based glycerolipids as antitumor agents.

Definition

ChEBI: An alkylglycerol that is glycerol carrying a single palmityl (hexadecyl) substituent at position 1.

InChI:InChI=1/C19H40O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-22-18-19(21)17-20/h19-21H,2-18H2,1H3

Upstream product

• 26459-58-5 allyl-1-hexadecyl ether 
• 20779-14-0 methanesulfonic acid hexadecyl ester 
• 100-79-8 (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol 
• 6068-28-6 tosylate de n-hexadecyle 
• 82002-21-9 2-O-Benzyl-1-O-hexadecyl-3-O-trityl-glycerin 
• 89496-73-1 4-(n-hexadecyloxymethyl)-2,2-dimethyl-1,3-dioxolane 
• 36653-82-4 1-Hexadecanol 
• 556-52-5 oxiranyl-methanol 
• 4860-03-1 1-Chlorohexadecan 
• 7647-01-0 hydrogenchloride 
• 91326-86-2 16-<(2S)-(2,3-(isopropylidenedioxy)propyl)oxy>hexadecane 
• 57-10-3 1-hexadecylcarboxylic acid 
• 56-81-5 glycerol 
• 112-82-3 hexadecanyl bromide 

Downstream Products

• 21994-82-1 1-O-hexadecyl-2,3-diacetylglycerol 
• 544-77-4 1-iodohexadecane 
• 56-81-5 glycerol 
• 946568-34-9 [1-(4,4'-dimethoxytrityl)]-3-hexadecylglycerol 
• 118469-68-4 1-(hexadecyloxy)-3-((4-methoxyphenyl)diphenylmethoxy)-2-propanol 
• 76-84-6 triphenylmethyl alcohol 
• 82002-20-8 1-O-hexadecyl-3-O-trityl-rac-glycerol 
• 92471-46-0 (R)-3-(1-hexadecyloxy)-1-(trityloxy)propan-2-ol 
• 1263034-20-3 C₃₉H₅₆O₅S 
• 133281-03-5 5-Heptadecyl-2-benzyloxymethyl-1,3-dioxolane 
• 133281-05-7 5-Hexadecyloxymethyl-2-benzyloxymethyl-1,3-dioxolane 
• 158268-05-4 1,2-Di-O-hexadecyl-3-O-tritylglycerol 
• 6076-35-3 1,2-dihexadecylglycerol 
• 131730-39-7 Toluene-4-sulfonate3-[5-(2-hexadecyloxymethyl-[1,3]dioxolan-4-ylmethoxycarbonyl)-pentyl]-thiazol-3-ium; 

Relevant articles and documents

NUCLEIC ACID OF FORMULA (I): GlXmGn, OR (II): ClXmCn, IN PARTICULAR AS AN IMMUNE-STIMULATING AGENT/ADJUVANT

The present invention relates to a nucleic acid of the general formula (I): GlXmGn, or (II): ClXmCn, which may be modified by a lipid. The nucleic acid of the invention acts as an immune-stimulating agent inducing the innate immune response. The invention relates further to a pharmaceutical composition (in a first embodiment), each containing an immune-stimulating agent according to the invention in combination with a pharmaceutically active carrier/vehicle (and, optionally, further auxiliary substances, additives and/or further adjuvants). In another embodiment, the inventive nucleic acid is combined with at least one pharmaceutically active component, a pharmaceutically acceptable carrier/vehicle (and, optionally, further auxiliary substances, additives and/or further adjuvants). Accordingly, the present invention is directed to a vaccine, which corresponds to a pharmaceutical composition of the invention (second embodiment), wherein the pharmaceutically active component induces a specific immune response (e.g. an antigen). The present invention relates likewise to the use of a nucleic acid of the invention or a pharmaceutical composition according to the invention for the treatment of infectious diseases, autoimmune diseases, allergies or cancer diseases.

Design, synthesis and cytotoxicity of chimeric erlotinib-alkylphospholipid hybrids

Two series of erlotinib-alkylphospholipid hybrids were prepared and evaluated for their antiproliferative activities against a panel of four cell lines representing lung, breast, liver and skin cancers using erlotinib and miltefosine as reference standards. Amide analogs elicited more enhanced cytotoxic activity than analogous esters. Amide derivatives 8d and 8e exhibited promising broad-spectrum antiproliferative activity and higher efficacy than reference erlotinib and miltefosine. Their cellular GI50 values was in the ranges of 24.7–46.9 μM and 26.8–43.1 μM for 8e and 8d respectively. Assay results of the inhibitory activity of the prepared compounds on EGFR kinase reaction and Akt phosphorylation in conjugation with statistical correlation analysis indicated that other mechanisms might contribute to their elicited cytotoxicities. In addition, statistical correlation analysis revealed that mechanisms of elicited cytotoxicities for amide series might be different from ester series. In addition, correlation analysis indicated variations in the mechanisms according to the types of cell line.

PROCESS FOR PREPARING A POLYOL ETHER

The present invention relates to a process for preparing a polyol ether of formula (I), comprising a step of reductive alkylation involving a compound of general formula (II) and a compound of general formula (III): in which R1, R2, R3 and R4 are as defined in claim 1.