103-98-0

Basic information

• Product Name: Dodecanamide, N-(4-hydroxyphenyl)-
• Synonyms: N-(4-hydroxyphenyl)dodecanamide;4-(Dodecanoylamino)phenol;N-(4-hydroxyphenyl)lauramide
• CAS NO: 103-98-0
• Molecular Formula: C₁₈H₂₉NO₂
• Molecular Weight: 291.42836
• EINECS: 203-164-3
• Mol File: 103-98-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 475.4°C at 760 mmHg
• Flash Point: 241.3°C
• Appearance: /
• Density: 1.018g/cm³
• Vapor Pressure: 1.16E-09mmHg at 25°C
• Refractive Index: 1.532
• CAS DataBase Reference: Dodecanamide, N-(4-hydroxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Dodecanamide, N-(4-hydroxyphenyl)-(103-98-0)
• EPA Substance Registry System: Dodecanamide, N-(4-hydroxyphenyl)-(103-98-0)

Safety Data

• Hazardous Substances Data: 103-98-0(Hazardous Substances Data)

Usage

General Description

Dodecanamide, N-(4-hydroxyphenyl)-, is a chemical compound with the molecular formula C18H29NO2. It consists of a dodecanamide (a type of fatty acid amide) molecule with a 4-hydroxyphenyl group attached to one of its nitrogen atoms.

InChI:InChI=1/C18H29NO2/c1-2-3-4-5-6-7-8-9-10-11-18(21)19-16-12-14-17(20)15-13-16/h12-15,20H,2-11H2,1H3,(H,19,21)

Upstream product

• 143-07-7 lauric acid 
• 103-90-2 4-acetaminophenol 
• 123-30-8 4-amino-phenol 
• 112-16-3 n-dodecanoyl chloride 
• 645-66-9 lauric anhydride 
• 21260-90-2 ethyl dodecanoyl carbonate 

Relevant articles and documents

Antioxidant and anticancer activities of novel p-alkylaminophenols and p-acylaminophenols (aminophenol analogues)

Novel compounds were designed based on fenretinide, N-(4-hydroxyphenyl)retinamide (2), which is a synthetic amide of all-trans-retinoic acid (1) that is a potent antioxidant and anticancer agent. Our recent findings indicated that antioxidant and anticancer activities were due to p-methylaminophenol moiety (8) in 2, and that p-octylaminophenol (7), which has an elongated alkyl chain, was more potent than 8. This finding lets us to investigate whether compounds containing alkyl or acyl chains linked to an aminophenol residue as long as 2 and 1, would show activities greater than 2. For this purpose, we prepared p-dodecanoylaminophenol (3), p-decanoylaminophenol (4), p-dodecylaminophenol (5), and p-decylaminophenol (6). The p-alkylaminophenols, 5 and 6, exhibited superoxide scavenging activities, but not p-acylaminophenols, 3 and 4. Elongation of the alkyl chain length reduced superoxide trapping capability (8 > 7 > 6 > 5). In contrast, lipid peroxidation in rat liver microsomes was reduced by 5 and 6 in dose-dependent manner. Compounds 3 and 4 were poor lipid peroxidation inhibitors, being approximately 400- to 1300-fold lower than 5 and 6. In addition, all compounds inhibited cell growth of human leukemia cell lines, HL60 and HL60R, in dose-dependent manners (5 > 6 > 3 = 4). The HL60R cell line is resistant against 1. Growth of both cell lines was suppressed by 5 and 6 in a fashion dependent on the length of the aminophenol alkyl chain, but not by 3 and 4. These results indicate that 5, a potent anticancer agent greater than 2, may potentially have clinical utility, and that its anticancer activity is correlated with inhibitory potency against lipid peroxidation, but not with superoxide scavenging activity.

Synthesis of Acetaminophen Analogues Containing α-Amino Acids and Fatty Acids for Inhibiting Hepatotoxicity

Acetaminophen is a popular antipyretic analgesic medicine that has weaker anti-inflammatory properties and lower incidence of side effects than nonsteroidal anti-inflammatory drugs (NSAIDs). However, acetaminophen causes hepatotoxicity due to the reactive metabolite N -acetyl- p -benzoquinone imine (NAPQI). We have obtained acetaminophen analogues in 57-99percent yields by using aniline derivatives with protected α-amino acids and fatty acids via the corresponding mixed carbonic carboxylic anhydrides in aqueous MeCN. We have also succeeded in synthesizing AM404 analogues in 76-97percent yields, which are expected to be promising candidates for reducing hepatotoxicity.

Corrosion inhibiting composition

A composition, in contact with a corrodable metal surface, which composition comprises: (a) an aqueous-based or oil-based system; and (b) as inhibitor for protecting the metal surface against corrosion, at least one compound having the formula I: STR1 as well as salts or partial esters thereof wherein: n is 0 or an integer ranging from 1 to 20, R is a straight or branched chain C4 -C30 alkyl group, optionally interrupted by one, two or three oxygen atoms or substituted by one, two or three hydroxy groups, a C5 -C12 cycloalkyl group, a C6 -C10 aryl group optionally substituted by one, two or three C1 -C12 alkyl groups, or a C7 -C13 aralkyl group which is optionally substituted by a hydroxyl group; R1 is H or a straight- or branched chain C1 -C4 alkyl group; R2 is H, a straight or branched chain C1 -C4 alkyl group or CO2 H; R3 is H, a straight or branched chain C1 -C4 alkyl group, --CH2 CO2 H or --CH2 CH2 CO2 H; R4 is H, a straight or branched chain C1 -C4 alkyl group or CO2 H; R5 is H, a straight or branched chain C1 -C4 alkyl group, CH2 CO2 H or CH2 CH2 CO2 H; provided that at least one group R4 must be CO2 H, with the provisio, that compositions comprising an oil-based system and a compound having the formula STR2 wherein R, R1 and R2 are hydrogen or alkyl radicals, having a total from 10 to 38 C-atoms, are excluded.