29400-43-9

Basic information

• Product Name: [S,(+)]-2-Amino-1-octadecanol
• Synonyms: (+)-Sphingine;(2S)-2-Amino-1-octadecanol;(S)-2-Aminooctadecane-1-ol;[S,(+)]-2-Amino-1-octadecanol;(2R)-2-Amino-1-octadecanol;(R)-2-Aminooctadecane-1-ol;[R,(-)]-2-Amino-1-octadecanol
• CAS NO: 29400-43-9
• Molecular Formula: C18H39 N O
• Molecular Weight: 0
• Mol File: 29400-43-9.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: [S,(+)]-2-Amino-1-octadecanol(CAS DataBase Reference)
• NIST Chemistry Reference: [S,(+)]-2-Amino-1-octadecanol(29400-43-9)
• EPA Substance Registry System: [S,(+)]-2-Amino-1-octadecanol(29400-43-9)

Safety Data

• Hazardous Substances Data: 29400-43-9(Hazardous Substances Data)

Upstream product

• 506-02-5 3-deoxydihydrosphingosine 
• 56-86-0 L-glutamic acid 
• 34227-75-3 (+)(R)-2-acetylamino-octadecanol-⁽¹⁾ 
• 76334-09-3 D-erythro-1-β-D-galactopyranosyloximethyl-2-tetracosanoylamino-octadecan-3-ol 
• 408336-86-7 1-acetoxy-octadecan-2-one 
• 40480-10-2 heptadecanoyl chloride 
• 492455-21-7 1-diazo-octadecan-2-one 
• 34227-76-4 (2R)-1-acetoxy-2-(acetylamino)octadecane 
• 214556-58-8 (4R_,1'Z)-3-(tert-butoxycarbonyl)-2_,2-dimethyl-4-(1'-hexadecenyl)oxazolidine 
• 528852-38-2 4-hexadecyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 

Downstream Products

• 54336-63-9 (R)-2-benzoylamino-octadecan-1-ol 
• 50886-78-7 (+/-)-2-benzoylamino-octadecanoic acid 
• 50886-78-7 (R)-2-benzoylamino-octadecanoic acid 

Relevant articles and documents

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(3Z)-2-Acetylamino-3-octadecen-1-ol as a potent apoptotic agent against HL-60 cells

(2R,3Z)-, (2R,3E)-, (2S,3Z) and (2S,3E)-2-Acetylamino-3-octadecen-1-ol, and (2R)- and (2S)-2-acetylamino-octadecan-1-ol were prepared using the Wittig olefination of Garner's aldehyde (N-Boc-N,O-isopropylidene-L- or D-serinal) from L- or D-serine. The apoptotic activities of these saturated and unsaturated 2-acetylaminoalcohols were examined in human leukemia HL-60 cells using MTT assay. Among the newly synthesized compounds, the cis-isomers were the most potent. Despite their simple structures, (2R,3Z)- and (2S,3Z)-2-acetylamino-3-octadecen-1-ol showed high and comparable apoptotic activities compared with N-acetyl-D-erythro-sphingosine (D-e-C2-Cer, a well-known inducer of apoptosis). Their apoptotic activities were in the order D-e-C2-Cer≈L-e-C2-Cer≈(2R,3Z)-≈(2S,3Z)-?(2R,3E)-≈(2S,3E)-≈(2R) -≈(2S)-derivative. Qualitative analysis of DNA fragmentation caused by these compounds was conducted using agarose gel electrophoresis, and typical DNA fragmentation was found in the cases of (2R,3Z)- and (2S,3Z)-isomers such as C2-Cer, but not trans and saturated isomers. The morphological features of the cells, the proteolytic processing of pro-caspase-3, and the cleavage of PARP as a result of exogenous treatment with (2R,3Z)- and (2S,3Z)-isomers indicated that cell death induced by these compounds was apoptosis. These observations suggest that these newly synthesized compounds, (3Z)-2-Acetylamino-3-octadecen- 1-ol, have similar characteristics and apoptosis-inducing activities against HL-60 cells with C2-Cer.