108695-25-6

Basic information

• Product Name: 2,4,6-Octatrienoic acid, 7-(3,4-dihydro-4,4-dimethyl-2H-1-benzopyran-6 -yl)-3-methyl-, (E,E,E)-
• Synonyms: 2,4,6-Octatrienoic acid, 7-(3,4-dihydro-4,4-dimethyl-2H-1-benzopyran-6 -yl)-3-methyl-, (E,E,E)-
• CAS NO: 108695-25-6
• Molecular Formula: C20H24 O3
• Molecular Weight: 0
• Mol File: 108695-25-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 495.8°Cat760mmHg
• Flash Point: 174.3°C
• Appearance: /
• Density: 1.074g/cm³
• Vapor Pressure: 1.2E-10mmHg at 25°C
• Refractive Index: 1.554
• CAS DataBase Reference: 2,4,6-Octatrienoic acid, 7-(3,4-dihydro-4,4-dimethyl-2H-1-benzopyran-6 -yl)-3-methyl-, (E,E,E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-Octatrienoic acid, 7-(3,4-dihydro-4,4-dimethyl-2H-1-benzopyran-6 -yl)-3-methyl-, (E,E,E)-(108695-25-6)
• EPA Substance Registry System: 2,4,6-Octatrienoic acid, 7-(3,4-dihydro-4,4-dimethyl-2H-1-benzopyran-6 -yl)-3-methyl-, (E,E,E)-(108695-25-6)

Safety Data

• Hazardous Substances Data: 108695-25-6(Hazardous Substances Data)

Usage

Molecular structure

Long-chain fatty acid derivative with a complex structure, containing a benzopyran ring and multiple double bonds.

Type of fatty acid

Potential polyunsaturated fatty acid due to the presence of multiple double bonds.

Potential properties

Antioxidant and anti-inflammatory properties due to the presence of 3-methyl and 3,4-dihydro-4,4-dimethyl substituents on the benzopyran ring.

Geometric configuration

The "E,E,E" designation indicates the specific geometric configuration of the double bonds, which may influence its biological activity and reactivity in chemical reactions.

Applications

Potential applications in pharmaceuticals, nutraceuticals, and functional foods due to its unique and bioactive nature.

InChI:InChI=1/C20H24O3/c1-14(12-19(21)22)6-5-7-15(2)16-8-9-18-17(13-16)20(3,4)10-11-23-18/h5-9,12-13H,10-11H2,1-4H3,(H,21,22)/b6-5+,14-12+,15-7+

Upstream product

• 108695-23-4 <3-(1,2,3,4-tetrahydro-4,4-dimethyl-6-chromanyl)-2-butenyl>triphenylphosphonium bromide 
• 108695-22-3 2-(4,4-Dimethyl-chroman-6-yl)-but-3-en-2-ol 
• 88579-19-5 4,4-Dimethylchroman-6-yl Methyl Ketone 
• 62054-49-3 ethyl (E)-3-formyl-2-butenoate 
• 108695-24-5 (2E,4E,6E)-7-(4,4-Dimethyl-chroman-6-yl)-3-methyl-octa-2,4,6-trienoic acid ethyl ester 

Relevant articles and documents

Heteroarotinoids as anticancer agents

Novel heteroarotinoid compositions characterized by the formulae: STR1 where: X is S or O; OAc is the acetate group STR2 and R is --H, --OH, --OCH3, or --OC2 H5 and includes STR3 for formulae (1) and (2). Such compositions exhibit activity as anticancer agents.

Heteroarotinoids. Synthesis, Characterization, and Biological Activity in Terms of an Assessment of These Systems To Inhibit the Induction of Ornithine Decarboxylase Activity and To Induce Terminal Differentiation of HL-60 Cells

The synthesis of certain heteroarotinoids has been achieved, namely the systems (2E,4E,6E)-3,7-dimethyl-7-(1,2,3,4-tetrahydro-4,4-dimethyl-6-thiochromanyl)-2,4,6-heptatrienoic acid (1a), ethyl (2E,4E,6E)-3,7-dimethyl-7-(1,2,3,4-tetrahydro-4,4-dimethyl-6-thiochromanyl)-2,4,6-heptatrienoate (1b), (2E,4E,6E)-3,7-dimethyl-7-(1,2,3,4-tetrahydro-4,4-dimethyl-6-chromanyl)-2,4,6-heptatrienoic acid (1c), 2-phthalimidoethyl 3,7-dimethyl-7-(1,2,3,4-tetrahydro-4,4-dimethyl-6-thiochromanyl)-2,4,6-heptatrienoate (1d), methyl (E)-p-benzoate (2a), (E)-p-benzyl alcohol (2b), (E)-p-benzonitrile (2c), (E)-p-benzaldehyde (2d), methyl 4-benzoate (3a), and (E)-p-benzoic acid (3b).Characterization via elemental, IR, 1H NMR, and 13C NMR analyses was completed for these heterocycles.The biological activity of these heteroarotinoids was assayed by either the suppression of the 12-O-tetradecanoylphorbol 13-acetate (TPA) induced synthesis of ornithine decarboxylase (ODC) in mouse skin or the induction of differentiation of human (HL-60) promyelocytic cells.In the ODC assay, system 1a-c exhibited strong activity (within 10percent of or less than the control) whereas alcohols 2b and 3a showed good activity (within 50percent of the control) as compared to either 13-cis-retinoic acid or trans-retinoic acid.Moderate activity was observed with 2a and 2b while 1d and 2c were essentially inactive.With the HL-60 assay, 1a and 1c were approximately 2- and 5-fold less active, respectively, than trans-retinoic acid.In contrast, 2a, 3a, and 3b inducted differentiation of only a very small percentage of the cells.Acids 1a and 1c were the most active heteroarotinoids in the two biological assays.Consequently, the presence of the heteroatom does not eradicate the activity of the heteroarotinoids and thus they may have potential as chemotherapeutic agents.