19855-42-6

Basic information

• Product Name: 2-[(2E,5E,7E,9R,10R,11E)-10-hydroxy-3,7,9,11-tetramethyltrideca-2,5,7,11-tetraen-1-yl]-5,6-dimethoxy-3-methylpyridin-4(1H)-one
• Synonyms: 2-[(2E,5E,7E,9R,10R,11E)-10-hydroxy-3,7,9,11-tetramethyltrideca-2,5,7,11-tetraen-1-yl]-5,6-dimethoxy-3-methylpyridin-4-ol; 4-pyridinol, 2-[(2E,5E,7E,9R,10R,11E)-10-hydroxy-3,7,9,11-tetramethyl-2,5,7,11-tridecatetraen-1-yl]-5,6-dimethoxy-3-methyl-
• CAS NO: 19855-42-6
• Molecular Formula: C₂₅H₃₇NO₄
• Molecular Weight: 415.5656
• Mol File: 19855-42-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 591.7°C at 760 mmHg
• Flash Point: 311.6°C
• Density: 1.05g/cm³
• Vapor Pressure: 1.83E-16mmHg at 25°C
• Refractive Index: 1.533
• CAS DataBase Reference: 2-[(2E,5E,7E,9R,10R,11E)-10-hydroxy-3,7,9,11-tetramethyltrideca-2,5,7,11-tetraen-1-yl]-5,6-dimethoxy-3-methylpyridin-4(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(2E,5E,7E,9R,10R,11E)-10-hydroxy-3,7,9,11-tetramethyltrideca-2,5,7,11-tetraen-1-yl]-5,6-dimethoxy-3-methylpyridin-4(1H)-one(19855-42-6)
• EPA Substance Registry System: 2-[(2E,5E,7E,9R,10R,11E)-10-hydroxy-3,7,9,11-tetramethyltrideca-2,5,7,11-tetraen-1-yl]-5,6-dimethoxy-3-methylpyridin-4(1H)-one(19855-42-6)

Safety Data

• Hazardous Substances Data: 19855-42-6(Hazardous Substances Data)

Upstream product

• 1112068-20-8 C₁₆H₁₉NO₄ 
• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 936482-98-3 (2E,4R,5R)-4-(tert-butyldimethylsilyloxy)-3,5-dimethyl-2-octen-6-yn 
• 131622-62-3 piericidin A₁ 3′-O-6-deoxy-α-L-talopyranoside 
• 50331-71-0 ethyl 3-methyl-2-oxobut-3-enoate 
• 497-03-0 2-methylbut-2-enal 
• 912877-19-1 (R)-4-benzyl-3-((2S,3R,E)-3-hydroxy-2,4-dimethylhex-4-enoyl)oxazolidin-2-one 
• 912877-18-0 2-[(Z)-Methanesulfonylimino]-3-methyl-but-3-enoic acid ethyl ester 
• 871316-24-4 tert-Butyl-[(3E,5E,8E)-(1R,2R)-9-iodo-2,4,8-trimethyl-1-((E)-1-methyl-propenyl)-nona-3,5,8-trienyloxy]-dimethyl-silane 
• 871316-18-6 2-(hydroxy-triisopropylsilanyl-methyl)-5,6-dimethoxy-3-methyl-pyridin-4-ol 
• 871316-29-9 2,3-dimethoxy-5-methyl-6-triisopropylsilanyloxymethyl-pyridin-4-ol 
• 871316-07-3 1-methanesulfonyl-5,5,6,6-tetramethoxy-3-methyl-1,4,5,6-tetrahydro-pyridine-2-carboxylic acid ethyl ester 

Downstream Products

• 5085-85-8 2-((2E,5E,7E,11E)-(9R,10S)-10-Hydroxy-3,7,9,11-tetramethyl-trideca-2,5,7,11-tetraenyl)-5,6-dimethoxy-3-methyl-pyridin-4-ol 

Relevant articles and documents

Polyketides and Anthranilic Acid Possessing 6-Deoxy-α- l -talopyranose from a Streptomyces Species

A bioassay-guided investigation in conjunction with chemical screening led to the isolation of three new glycosides, ulleungoside (1), 2-methylaminobenzoyl 6-deoxy-α-l-talopyranoside (2), and naphthomycinoside (3), along with three known secondary metabolites (5-7) from Streptomyces sp. KCB13F030. Their structures were elucidated by detailed NMR and MS spectroscopic analyses. Absolute configurational analysis of the sugar units based on the magnitudes of the coupling constants, NOESY correlations, chemical derivatization, and optical rotation measurements revealed that compounds 1-3 and 5 incorporate the rare deoxyhexose 6-deoxy-α-l-talopyranose. The absolute configuration of a polyketide extender unit of 3 was determined by applying the J-based configuration analysis and modified Mosher's method. Ulleungoside (1) and naphthomycin A (7) showed in vitro inhibitory effects against indoleamine 2,3-dioxygenase activity. Further bioevaluation revealed that compounds 1 and 7 had moderate antiproliferative activities against several cancer cell lines, and compounds 5 and 6, which are members of the piericidin family, induced autophagosome accumulation.

Total synthesis of piericidin A1. application of a modified negishi carboalumination-nickel-catalyzed cross-coupling

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Total synthesis of piericidin A1 and B1 and key analogues

Full details of the total synthesis of piericidin A1 and B1 and its extension to the preparation of a series of key analogues are described including ent-piericidin A1 (ent-1), 4′-deshydroxypiericidin A1 (58), 5′-desmethylpiericidin A1 (73), 4′-deshydroxy-5′- desmethylpiericidin A1 (75), and the corresponding analogues 51, 59, 76, and 77 bearing a simplified farnesyl side chain. The evaluation of these key analogues, along with those derived from their further functionalizations, permitted a scan of the key structural features providing new insights into the role of the substituents found in both the pyridyl core as well as the side chain. A strategic late stage heterobenzylic Stille cross-coupling reaction of the pyridyl core with the fully elaborated side chain permitted ready access to the analogues in which each half of the molecule could be systematically and divergently modified. The pyridyl cores were assembled enlisting inverse electron demand Diels-Alder reactions of N-sulfonyl-1-azabutadienes, while key elements of side chain syntheses include an anti selective asymmetric aldol to install the C9 and C10 relative and absolute stereochemistry (for natural and ent-1) and a modified Julia olefination for formation of the C5-C6 trans double bond with convergent assemblage of the side chains.