145411-41-2

Basic information

• Product Name: Hexacosanoyl chloride
• Synonyms: Hexacosanoylchlorid;ceroyl chloride;hexacosanoic acid chloride;cerotyl chloride
• CAS NO: 145411-41-2
• Molecular Formula: C26H51ClO
• Molecular Weight: 415.143
• Mol File: 145411-41-2.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 425.5±8.0 °C(Predicted)
• Density: 0.890±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Hexacosanoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Hexacosanoyl chloride(145411-41-2)
• EPA Substance Registry System: Hexacosanoyl chloride(145411-41-2)

Safety Data

• Hazardous Substances Data: 145411-41-2(Hazardous Substances Data)

Usage

Uses

Hexacosanoyl Chloride is a reagent in the synthesis of aglycoside analog of immunostimulant galactosylceramide (KRN7000) via diastereoselective alkenylalane addn. and epoxidn./carbamate ring opening

Upstream product

• 506-46-7 1-hexacosanoic acid 

Downstream Products

• 6624-81-3 1-cyclohexyloxy-hexatriacontan-11-one 
• 906652-18-4 Hexacosanoic acid {(1S,2S,3R)-2,3-dihydroxy-1-[2-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-heptadecyl}-amide 
• 906652-19-5 Hexacosanoic acid {(1S,2R,3S)-2,3-dihydroxy-1-[2-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-heptadecyl}-amide 
• 1233218-92-2 C₇₉H₁₂₁NO₈ 
• 158021-47-7 KRN₇₀₀₀ 
• 205371-71-7 cerotic acid para-nitrophenyl ester 
• 1435266-79-7 (2S,3S,4R)-3,4-di-O-benzyl-2-hexacosanamido-1-O-(2,3,4-tri-O-benzyl-6-O-methoxymethyl-α-D-galactopyranosyl)octadecane-1,3,4-triol 
• 1435266-88-8 (2S,3S,4R)-3,4-di-O-benzyl-2-hexacosanamido-1-O-[2,3,4-tri-O-benzyl-6-O-(2-benzyloxyethyl)-α-D-galactopyranosyl]octadecane-1,3,4-triol 
• 1435266-83-3 (2S,3S,4R)-3,4-di-O-benzyl-2-hexacosanamido-1-O-[2,3,4-tri-O-benzyl-6-O-(2-methoxyethoxymethyl)-α-D-galactopyranosyl]octadecane-1,3,4-triol 

Relevant articles and documents

Synthesis of a 2 -Deoxy-β-GalCer

Structural studies of ternary complexes of CD1d/glycosyl ceramides/iNKT cells and CD1d/sulfatide/sulfatide reactive Type II NKT cells have shown how the polar moieties on the glycolipids interact with both the antigen presenting protein (CD1d) and the T cell receptors. However, these structures alone do not reveal the relative importance of these interactions. This study focuses on the synthesis of the previously unknown 2''-deoxy-β-galactosyl ceramide 2. This glycolipid is also evaluated for its ability to stimulate iNKT cells and sulfatide-reactive Type II NKT cells.

RCAI-133, an N-methylated analogue of KRN7000, activates mouse natural killer T cells to produce Th2-biased cytokines

We synthesized seven new analogues of KRN7000: RCAI-133 and 154-159. RCAI-154, 156 and 158 are secondary-amide analogues having a hydroxy, a methyl or two methyl groups at the α-position of a linear C18-acyl chain, respectively. RCAI-155, 157 and 159 are corresponding N-methylated tertiary amide analogues, and RCAI-133 is the N-methylated KRN7000. Among them, a PBS solution of RCAI-133 induced mouse lymphocytes to produce Th2-biasing cytokines in vivo, while RCAI-154-159 showed only weak or almost no immunostimulatory activity. Therefore, N-methylation led the glycolipid to produce predominantly Th2-type cytokines, while acyl α-substitution was detrimental to activity.

A practical and scalable synthesis of KRN7000 using glycosyl iodide as the glycosyl donor

KRN7000 is particularly useful because it is a powerful and specific CD1d agonist and has prompted intense interest in the context of immunology in the past 25 years. Its limited commercial availability and high price has led to the publication of many different syntheses. However, almost all of them focused on the methodology development rather than a scalable synthesis. Herein, we have described a practical and scalable procedure for the synthesis of KRN7000 basing on the glycosyl iodide method. This procedure involves total of eight steps to obtain the highly pure product KNR7000 on gram scale from the commercially available starting materials (d-galactose and the phytosphingosine) with only three column chromatographic purifications.