41442-57-3

Basic information

• Product Name: 5-N-HEPTADECYLRESORCINOL
• Synonyms: 5-N-HEPTADECYLRESORCINOL;5-Heptadecylbenzene-1,3-diol;5-Heptadecyl-1,3-benzenediol;5-Heptadecyl-1,3-dihydroxybenzene
• CAS NO: 41442-57-3
• Molecular Formula: C₂₃H₄₀O₂
• Molecular Weight: 348.5625
• Mol File: 41442-57-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 478°Cat760mmHg
• Flash Point: 202.6°C
• Appearance: /
• Density: 0.95g/cm³
• Vapor Pressure: 9.24E-10mmHg at 25°C
• Refractive Index: 1.506
• Storage Temp.: 2-8°C
• BRN: 2287460
• CAS DataBase Reference: 5-N-HEPTADECYLRESORCINOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-N-HEPTADECYLRESORCINOL(41442-57-3)
• EPA Substance Registry System: 5-N-HEPTADECYLRESORCINOL(41442-57-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 41442-57-3(Hazardous Substances Data)

Usage

Uses

5-Heptadecylresorcinol may be used as an analytical reference standard for the quantification of the analyte in mango peels, rye grains and agricultural products using different chromatography techniques.

General Description

5-Heptadecylresorcinol belongs to the group of alk(en)ylresorcinols (ARs), exhibiting pharmacological properties such as anti-inflammatory, anti-carcinogenic and anti-microbial bioactivities. It is most commonly found in cereals such as barley, spelt, wheat, rye, ginkgo, mango peels, pulp, peas, etc.

InChI:InChI=1/C23H40O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21-18-22(24)20-23(25)19-21/h18-20,24-25H,2-17H2,1H3

Upstream product

• 41395-17-9 1,3-dimethoxy-5-heptadecylbenzene 
• 524-14-1 S-(hydrogen malonyl)coenzyme A 
• 17213-57-9 3,5-dimethoxybenzoyl chloride 
• 872-26-4 hexadecylmagnesium bromide 
• 52483-25-7 1-(3',5'-Dimethoxyphenyl)heptadecan-1-ol 

Downstream Products

• 1108148-88-4 [2,4,6-2H₃]-5-heptadecylresorcinol 

Relevant articles and documents

Synthesis and inhibitory activities against colon cancer cell growth and proteasome of alkylresorcinols

We have identified alkylresorcinols (ARs) as the major active components in wheat bran against human colon cancer cell growth (HCT-116 and HT-29) using a bioassay-guided approach. To further study the structure-activity relationships, 15 ARs and their intermediates (1-15) were synthesized expediently by the modified Wittig reaction in aqueous media, and six 5-alkylpyrogallols and their analogues (16-21) were prepared by the general Grignard reaction. The synthetic AR analogues were evaluated for activities against the growth of human colon cancer cells HCT-116 and HT-29 and the chymotrypsin-like activity of the human 20S proteasome. Our results found that (1) AR C13:0 and C15:0 (13 and 14) had the greatest inhibitory effects in human colon cancer cells HCT-116 and HT-29, while decreasing or increasing the side chain lengths diminished the activities; (2) two free meta-hydroxyl groups at C-1 and C-3 on the aromatic ring of the AR analogues greatly contributed to their antitumor activity; (3) the introduction of a third hydroxyl group at C-2 (20 and 21) into the aromatic ring of the AR analogues yielded no significant enhancement in activity against HCT-116 cells and decimated the effects against HT-29 cells, but dramatically increased the activity against the chymotrypsin-like activity of the human 20S proteasome; and (4) AR C11:0 (12) was found to have the greatest effect in a series of AR C9:0-C17:0 against the chymotrypsin-like activity of the human 20S proteasome.

An expedient synthesis of 5-n-alkylresorcinols and novel 5-n-alkylresorcinol haptens

The first synthesis of bioactive long alkyl chain 5-n-alkylresorcinols, present in whole grain products, by a novel modification of the Wittig reaction is described. All the main long chain 5-n-alkylresorcinols present in rye and wheat, including C23 and C25 analogues and haptens, which have not been previously prepared, were synthesised. Microwave-promoted reactions of a semistabilized ylid and alkanals in water gave good yields in both pressurized and open systems. An alternative microwave-promoted synthesis starting from non-stabilized alkyltriphenylphosphonium salts and 3,5-dimethoxybenzaldehyde worked as well. Aqueous media were suitable for the reactions even if the starting materials were not soluble in water. The 5-n-alkylresorcinols are potential biomarkers of whole grain intake, and the new hapten derivatives of 5-n-alkylresorcinols will open the way for the immunochemical detection techniques of alkylresorcinols.