26187-80-4

Usage

Uses

Used in Pharmaceutical Industry:
(2E,6E)-8-Hydroxy-2,6-dimethyl-2,6-octadienoic acid is used as a bioactive compound for its potential therapeutic applications. Its unique structure and properties make it a candidate for the development of new drugs, particularly in the area of natural product chemistry.
Used in Biochemical Research:
In the field of biochemistry, (2E,6E)-8-Hydroxy-2,6-dimethyl-2,6-octadienoic acid is utilized for studying the interactions of hydroxy fatty acids with biological systems. Its presence in certain plants provides a basis for investigating its role in plant biochemistry and potential applications in plant-derived pharmaceuticals.
Used in Natural Product Chemistry:
(2E,6E)-8-Hydroxy-2,6-dimethyl-2,6-octadienoic acid is employed as a key component in the exploration of natural products for novel chemical entities. Its characteristic properties and occurrence in plants make it a valuable subject for research aimed at discovering new bioactive compounds with potential applications in medicine and healthcare.

Upstream product

• 37905-02-5 (2E,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate 
• 83852-61-3 (2E,6E)-8-acetoxy-2,6-dimethylocta-2,6-dienoic acid 
• 38290-51-6 (2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienal 
• 106-24-1 Geraniol 
• 1326304-00-0 (2E,6E)-8-β-D-glucopyranosyloxy-2,6-dimethyl-2,6-octadienoic acid 
• 147612-81-5 (E)-(S)-2,6-Dimethyl-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-octa-2,7-dienoic acid 
• 105-87-3 3,7-dimethyl-2E,6-octadien-1-yl acetate 
• 144963-45-1 acaciagenin A 
• 144262-69-1 acaciaside A permethylate 
• 144262-68-0 (E)-(S)-2,6-Dimethyl-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-octa-2,7-dienoic acid methyl ester 

Downstream Products

• 108194-33-8 (2E,6E)-8-(2,5-Dihydroxy-3,4-dimethoxy-6-methyl-phenyl)-2,6-dimethyl-octa-2,6-dienoic acid 
• 98983-38-1 6-<7-carboxy-3-methyl-(2E,6E)-2,6-octadienyl>-2,3-dimethoxy-5-methyl-1,4-benzoquinone 
• 19891-75-9 16,16'-dihydroxylycopene 
• 40772-85-8 (2E,6E-dimethylocta-2,6-dienoic acid methyl ester)triphenylphosphonium bromide 
• 67517-34-4 [5-((2E,6E)-8-Chloro-3,7-dimethyl-octa-2,6-dienyl)-2,6,6-trimethyl-cyclohex-1-enyl]-acetonitrile 
• 67517-30-0 (2E,6E)-8-(3-Cyanomethyl-2,2,4-trimethyl-cyclohex-3-enyl)-2,6-dimethyl-octa-2,6-dienoic acid methyl ester 
• 67517-33-3 [5-((2E,6E)-8-Hydroxy-3,7-dimethyl-octa-2,6-dienyl)-2,6,6-trimethyl-cyclohex-1-enyl]-acetonitrile 

Relevant academic research and scientific papers

Iridoid and acyclic monoterpene glycosides, kankanosides L, M, N, O, and P from Cistanche tubulosa

Three iridoid glycosides, kankanosides L, M, and N, and two acyclic monoterpene glycosides, kankanosides O and P, were isolated from fresh stems of Cistanche tubulosa (Orobanchaceae) together with eight iridoid glycosides, five acyclic monoterpene glycosides, three phenylpropanoid glycosides, and four lignan glycosides. Their structures were elucidated on the basis of chemical and physicochemical evidence.

Structure-Odor Relationship Study on Geraniol, Nerol, and Their Synthesized Oxygenated Derivatives

Despite being isomers having the same citrus-like, floral odor, geraniol, 1, and nerol, 3, show different odor thresholds. To date, no systematic studies are at hand elucidating the structural features required for their specific odor properties. Therefore, starting from these two basic structures and their corresponding esters, namely, geranyl acetate, 2, and neryl acetate, 4, a total of 12 oxygenated compounds were synthesized and characterized regarding retention indices (RI), mass spectrometric (MS), and nuclear magnetic resonance (NMR) data. All compounds were individually tested for their odor qualities and odor thresholds in air (OT). Geraniol, the Z-isomer, with an OT of 14 ng/L, was found to be more potent than its E-isomer, nerol, which has an OT of 60 ng/L. However, 8-oxoneryl acetate was the most potent derivative within this study, exhibiting an OT of 8.8 ng/L, whereas 8-oxonerol was the least potent with an OT of 493 ng/L. Interestingly, the 8-oxo derivatives smell musty and fatty, whereas the 8-hydroxy derivatives show odor impressions similar to those of 1 and 3. 8-Carboxygeraniol was found to be odorless, whereas its E-isomer, 8-carboxynerol, showed fatty, waxy, and greasy impressions. Overall, we observed that oxygenation on C-8 affects mainly the odor quality, whereas the E/Z position of the functional group on C-1 affects the odor potency.

Methods for synthesis of carotenoids, including analogs, derivatives, and synthetic and biological intermediates

A method for synthesizing intermediates for use in the synthesis of carotenoid synthetic intermediates, carotenoid analogs, and/or carotenoid derivatives. The carotenoid analog, derivative, or intermediate may be administered to a subject for the inhibition and/or amelioration of any disease that involves production of reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals. In some embodiments, the invention may include methods for synthesizing chemical compounds including an analog or derivative of a carotenoid. Carotenoid analogs or derivatives may include acyclic end groups. In some embodiments, a carotenoid analog or derivative may include at least one substituent. The substituent may enhance the solubility of the carotenoid analog or derivative such that the carotenoid analog or derivative at least partially dissolves in water.

METHODS FOR SYNTHESIS OF CHIRAL INTERMEDIATES OF CAROTENOIDS, CAROTENOID ANALOGS, AND CAROTENOID DERIVATIVES

A method used for synthesizing intermediates for use in the synthesis of carotenoids and carotenoid analogs, and/or carotenoid derivatives. In some embodiments, the invention includes methods for synthesizing optically active intermediates useful for the synthesis of optically active carotenoids.

Efficient total synthesis of lycophyll (ψ,ψ-carotene-16,16′- diol)

A practical procedure is described for the total synthesis of lycophyll (16,16′-dihydroxy-lycopene; ψ,ψ-carotene-16,16′-diol), based on a C10 + C20 + C10 synthetic methodology using the commercially available materials geraniol (C10) and crocetin-dialdehyde (C20). A late-stage double Wittig olefination on crocetindialdehyde was used to form the desired lycophyll scaffold in eight linear synthetic steps, while generating a mixture of polyenic geometric isomers that could be effectively separated using HPLC. All-trans lycophyll was subsequently separated to >95% purity by semipreparative chromatography using a C30 carotenoid column.

Synthesis of 10-cyanoverticillene and its reactions directed toward the verticillol synthesis

Directed toward the synthesis of verticillols, 10-cyanoverticillene 8 was settled as a key intermediate. Bond formation of cyano chloride 7 possessing secoverticillane skeleton to the key intermediate 8 with LiN(TMS)2 at 60°C proceeded smoothly

Structure elucidation of two acylated triterpenoid bisglycosides from Acacia auriculiformis Cunn.

Acaciasides A and B, two novel acylated triterpenoid bisglycosides isolated from the fruits of Acacia auriculiformis, were respectively defined to be 3-O-[β-D-glucopyranosyl (1 → 6) {α-L-arabinopyranosyl (1 → 2)}-β-D-glucopyranosyl]-21-O-{6' S)-2'-trans-2',6'-dimethyl-6'-O-β-D-glucopyranosyl-2',7'- octadienoyl} acacic acid 28-O-α-L-rhamnopyranosyl (1 → 6) [β-D-xylopyranosyl (1 → 2)]-β-D-glucopyranoside (1) and 3-O-[β-D-glucopyranosyl (1 → 6) {α-L-arabinopyranosyl (1 → 2)}-β-D-glucopyranosyl]-21-O-[(6' S)-2'-trans-2',6'-dimethyl-6'-O-{β-D-xylopyranosyl (1 → 2)-β-D-glucopyranosyl}-2',7'-octadienoyl] acetic acid 28-O-α-L-rhamnopyranosyl (1 → 6) [β-D-xylopyranosyl (1 → 2)]-β-D-glucopyranoside (2). The structural details were elucidated by a combination of fast-atom-bombardment mass spectrometry, 1H-, and 13C NMR spectroscopy, and some chemical transformations.