DIENOIC ACID

CAS NO.: 626-99-3
EC/LİST NO. : 210-976-1

A new phytotoxic sesquiterpenoid penta-2,4- dienoic acid, named pyrenophoric acid, was isolated from solid wheat seed culture of Pyrenophora semeniperda, a fungal pathogen proposed as a mycoherbicide for biocontrol of cheatgrass (Bromus tectorum) and other annual bromes. 
These bromes are serious weeds in winter cereals and also on temperate semiarid rangelands. 
Dienoic acid was characterized as (2Z,4E)-5-[(7S,9S,10R,12R)-3,4-dihydroxy2,2,6-trimethylcyclohexyl)]-3-methylpenta-2,4-dienoic acid by spectroscopic and chemical methods. 
The relative stereochemistry of pyrenophoric acid was assigned using 1 H,1 H couplings and NOESY experiments, while its absolute configuration was determined by applying the advanced Mosher’s method. 
Pyrenophoric acid is structurally quite closely related to the plant growth regulator abscisic acid. 
When bioassayed in a cheatgrass coleoptile elongation test at 10−3 M, pyrenophoric acid showed strong phytotoxicity, reducing coleoptile elongation by 51% relative to the control. 
In a mixture at 10−4 M, its negative effect on coleoptile elongation was additive with that of cytochalasin B, another phytotoxic compound found in the wheat seed culture extract of this fungus, demonstrating that the extract toxicity observed in earlier studies was due to the combined action of multiple phytotoxic compounds.

Dienoic acids and pentadienyl alcohols are coupled in a decarboxylative and dehydrative manner at ambient temperature using
Pd(0) catalysis to generate 1,3,6,8-tetraenes. 
Contrary to related decarboxylative coupling reactions, an anion-stabilizing group is
not required adjacent to the carboxyl group. 
Of mechanistic importance, it appears that both the diene of the acid and the diene of
the alcohol are required for this reaction. 
To further understand this reaction, substitutions at every unique position of both coupling partners was examined and two potential mechanisms are presented.

The construction of sp2–sp3 carbon–carbon bonds remains a difficult and important problem in organic synthesis. 
Cross-coupling reactions provide avenues to these otherwise difficult reactions, but often require prefunctionalization of the coupling partners [1-9]. 
However, recent C–H activation research has enabled the use of further simplified starting materials

Another approach to the formation of C–C bonds is through decarboxylative coupling reactions . 
This can be arrived in a one-component fashion via the removal of CO2 from an ester or in a two-component manner by removal of CO2 from a carboxylic acid and coupling this to a substrate with a benzylic or allylic leaving group

Typical Pd(0)-catalyzed decarboxylative coupling reactions utilize an allylic or benzylic ester with either an anion-stabilizing group adjacent to the carboxyl group (i.e., carbonyl , nitrile , nitro , or alkyne ), or use an aryl carboxylate which typically requires the assistance of silver or copper(I) salts for the decarboxylative step. 
Dienoic acid is rare to use a pentadienyl electrophile, or to have a diene or simple alkene adjacent to the carboxyl group . 
Despite the absence of this type of reactivity, the decarboxylative coupling of a pentadienyl ndienoate was desirable enough for our group’s synthesis of clinprost that we attempted the reaction .
Fortunately, this coupling reaction was successfully employed in our reported nine-step synthesis of clinprost . 
A structurally related compound reacted similarly, however, the sorbate derivative  was low yielding with the majority of the material only rearranging to the linear ester. 
In all three of these cases, we never observed the more stable, fully conjugated tetraene. 
”Skipped diene” motifs are found in various natural products and there are few methods available to prepare these dienes. 
Skipped tetraene systems have even fewer methods for their synthesis , which makes the method described herein even more valuable.

Involved in the degradation of carbazole, a toxic N-heterocyclic aromatic compound containing dibenzopyrrole system. 
Catalyzes the hydrolytic cleavage of a carbon-carbon bond of 2-hydroxy-6-oxo-6-(2'-aminophenyl)hexa-2,4-dienoic acid (HOPDA) to yield anthranilate. 
CarC is specific for 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid (6-phenyl-HODA), and has little activity toward 2-hydroxy-6-oxohepta-2,4-dienoic acid and 2-hydroxymuconic semialdehyde. 
The effect of the presence of an amino group or hydroxyl group at the 2'-position of phenyl moiety of 6-phenyl-HODA on the enzyme activity is found to be small.

Cyclization of 4,8-dimethylnona-3,7-dienoic acid (homogeranic acid) in the presence of stannic chloride was studied under various conditions. 
Cyclization product obtained comprises 88 per cent trans- and 12 per cent cis-hexahydro-4,4,7a-trimethyl-2(3H)benzofuranone (trans- and cis-tetrahydroactinidiolide). 
Other products, such as monocyclic compounds, could not be detected in the reaction mixture. 
Isomerization of the trans isomer to the cis isomer in the presence of stannic chloride was also observed. 
Dienoic acid may be concluded that the cyclization reaction proceeds by a concerted mechanism.

Dienoic acid is any mono-carboxylic acid with an unbranched chain of ten carbon atoms, connected by seven single bonds and two double bonds. 
That is, any compound with formula HO(O=)C–(CH2)x–CH=CH–(CH2)y–CH=CH–(–CH2)z–H where x, y, and z can be zero or more, and x+y+z = 5 (72 isomers); or HO(O=)C–(CH2)r–CH=C=CH–(CH2) s–H where r + s = 6 (15 isomers). 
All these compounds have the formula C10H16O2. 
A salt or ester of such an acid is called a decadienoate.

The various decadienoic acid isomers can be distinguished by the positions of their double bonds along the chain. 
A double bond is said to be at position k if it connects carbons k and k+1 of the chain, counting from 1 at the carboxyl end. 
The positions are x+2 and x+y+4 for the first type (21 possibilities), and r+2 and r+3 for the second type (7 possibilities). 
The systematic name of the acid is formed by prefixing the positions of the double bonds to "decadienoic" or inserting them before the "dienoic" suffix. 
as in "4,7-decadienoic" or "dec-4,7-dienoic" for HO(O=)C–(–CH2)2–CH=CH–CH2–CH=CH–(CH2)2–H.

Dienoic acids with the two double bonds in the same positions can be further distinguished by the geometry of the adjacent single bonds.

Each double bond that is adjacent to two single C–C bonds can be in two cis-trans conformations, namely with those two single bonds on the same side (cis or Z) or opposite sides (trans or E) of the double bond's plane.

If the two double bonds overlap forming an allene core C=C=C surrounded by two single C–C bonds, the chain fragments C–C=C=C and C=C=C–C will lie on perpendicular planes.
Then, instead of cis-trans isomers, there will be two axial isomers distinguished by the handedness of the C–C=C=C–C "screw". 
They are denoted by the letters R and S.

Double bonds at the very end of the chain (–C=CH2 or -C=C=CH2) will not cause geometric isomerism, because the two hydrogen atoms in the final carbon are symmetrically placed relative to the bond's plane. 
However, geometric isomerism may still occur at that position in derivative compounds where one or both terminal hydrogens are replaced by different groups.

Formula:C20H36O2
MW:308.5
Purity:    ≥98% (TLC)
Appearance:Pale yellow oil.
Solubility:Soluble in ethanol or DMSO.
Shipping:Ambient
Long Term Storage:-20°C
Use/Stability:    Store, as supplied, at -20°C for up to 1 year. 
Store solutions at -20°C or colder for up to 1 month. Protect from oxidation.

Dienoic acid  or microbially derived surfactants are amphiphilic molecules of bacterial, fungal, or yeast origin, that exhibit excellent surface-activity, structural diversity, and environmental compatibility . 
Dienoic acid  promotes the uptake of poorly soluble substrates, heavy metal binding, modulates the immune response, and act as antimicrobial compounds . 
Application of Dienoic acid  as anti-biofilm agents has been explored widely in recent times against several bacterial and fungal species . 
Under specific testing conditions, BS has been reported to be efficacious than many traditional inhibitory and disruptive strategies against biofilms . 
In general terms, BS are thought to achieve the anti-biofilm effect through alteration of surface energy and surface wettability . 
Glycolipids are BS consisting of a carbohydrate linked to an aliphatic or hydroxy-aliphatic acid. 
Among them, the best known are rhamnolipids (RLs), which includes di- or mono-rhamnose sugars linked to a hydroxy fatty acid chain.

A new phytotoxic sesquiterpenoid dienoic acid, named pyrenophoric acid, was isolated from solid wheat seed culture of Pyrenophora semeniperda, a fungal pathogen proposed as a mycoherbicide for biocontrol of cheatgrass (Bromus tectorum) and other annual bromes. 
These bromes are serious weeds in winter cereals and also on temperate semiarid rangelands. Pyrenophoric acid was characterized as (2Z,4E)-5-[(7S,9S,10R,12R)-3,4-dihydroxy-2,2,6-trimethylcyclohexyl)]-3-methylpenta-2,4-dienoic acid by spectroscopic and chemical methods. 
The relative stereochemistry of pyrenophoric acid was assigned using 1H,1H couplings and NOESY experiments, while its absolute configuration was determined by applying the advanced Mosher’s method. Pyrenophoric acid is structurally quite closely related to the plant growth regulator abscisic acid. 
When bioassayed in a cheatgrass coleoptile elongation test at 10–3 M, pyrenophoric acid showed strong phytotoxicity, reducing coleoptile elongation by 51% relative to the control. In a mixture at 10–4 M, its negative effect on coleoptile elongation was additive with that of cytochalasin B, another phytotoxic compound found in the wheat seed culture extract of this fungus, demonstrating that the extract toxicity observed in earlier studies was due to the combined action of multiple phytotoxic compounds.

A new phytotoxic sesquiterpenoid dienoic acid, named pyrenophoric acid, was isolated from solid wheat seed culture of Pyrenophora semeniperda, a fungal pathogen proposed as a mycoherbicide for biocontrol of cheatgrass (Bromus tectorum) and other annual bromes. 
These romes are serious weeds in winter cereals and also on temperate semiarid rangelands. 
dienoic acid was characterized as (2Z,4E)-5-[(7S,9S,10R,12R)-3,4-dihydroxy2,2,6-trimethylcyclohexyl)]-3-methylpenta-2,4-dienoic acid by spectroscopic and chemical methods.
The relative stereochemistry of pyrenophoric acid was assigned using 1 H,1H couplings and NOESY experiments, while its absolute configuration was determined by applying the advanced Mosher’s method. 
dienoic acid is structurally quite closely related to the plant growth regulator abscisic acid. 
When bioassayed in a cheatgrass coleoptile elongation test at 10−3 M, pyrenophoric acid showed strong phytotoxicity, reducing coleoptile elongation by 51% relative to the control. 
In a mixture at 10−4 M, its negative effect on coleoptile elongation was additive with that of cytochalasin B, another phytotoxic compound found in the wheat seed culture extract of this fungus, demonstrating that the extract toxicity observed in earlier studies was due to the combined action of multiple phytotoxic compounds.

Substituted hexa-3,5-dienoic acid methyl esters  were conveniently prepared in one step by 1,2-carbonyl transposition of the corresponding dienones  using lead(IV) acetate and boron trifluoride–diethyl ether in benzene at room temperature.

A new phytotoxic sesquiterpenoid dienoic acid, named pyrenophoric acid, was isolated from solid wheat seed culture of Pyrenophora semeniperda, a fungal pathogen proposed as a mycoherbicide for biocontrol of cheatgrass (Bromus tectorum) and other annual bromes. 
These bromes are serious weeds in winter cereals and also on temperate semiarid rangelands. 
dienoic acid was characterized as (2Z,4E)-5-[(7S,9S,10R,12R)-3,4-dihydroxy- 2,2,6-trimethylcyclohexyl)]-3-methylpenta-2,4-dienoic acid by spectroscopic and chemical methods. The relative stereochemistry of pyrenophoric acid was assigned using 1H,1H couplings and NOESY experiments, while its absolute configuration was determined by applying the advanced Mosher’s method. 
dienoic acid is structurally quite closely related to the plant growth regulator abscisic acid.
When bioassayed in a cheatgrass coleoptile elongation test at 10-3 M, pyrenophoric acid showed strong phytotoxicity, reducing coleoptile elongation by 51% relative to the control. 
In a mixture at 10-4 M, its negative effect on coleoptile elongation was additive with that of cytochalasin B, another phytotoxic compound found in the wheat seed culture extract of this fungus, demonstrating that the extract toxicity observed in earlier studies was due to the combined action of multiple phytotoxic compounds.

Low dienoic acid content of the tissues of rats has been produced in two ways:
(a) withdrawal of essential fatty acid from the diet, and (b) exclusion of pyridoxine or thiamine from the diet or severe restriction of food (caloric deficiency).

A chemical structure of a molecule includes the arrangement of atoms and the chemical bonds that hold the atoms together. 
The dienoic acid molecule contains a total of 12 bond(s) There are 6 non-H bond(s), 3 multiple bond(s), 2 rotatable bond(s), 3 double bond(s), 1 carboxylic acid(s) (aliphatic) and 1 hydroxyl group(s).

Dienoic acid , a group of filamentous fungi, can invade and infect keratinized tissues of humans and animals, causing dermatophytosis. 
Dienoic acid  is one of the most common superficial fungal infections affecting about a quarter of the global population . 
Even though it does not lead to mortality, it causes significant morbidity apart from posing a critical public health problem, especially in tropical and subtropical developing countries like India. 
In these regions, the hot and humid climate favors the acquisition and maintenance of the disease . 
In several parts of the world, about 90 % of cases of chronic dermatophytosis have been attributed to Trichophyton spp. 
Again, treatment failure with antifungals is increasingly reported, especially in patients infected with T. rubrum, which, among other factors, can largely be attributed to biofilm formation . 
Dienoic acid  are of critical importance because they are implicated in a significant proportion of all clinical infections interfering with medicinal therapy . 

Dienoic acid  are incredibly resistant to most of the clinically used antimicrobials with inhibitory concentrations being 100-fold higher than that needed to inhibit planktonic cells . 
Contributing factors for such resistance include structural complexity, extracellular matrix (ECM), intrinsic metabolic heterogeneity, and biofilm-associated up-regulation of efflux pump genes . 
The Dienoic acid  ability of dermatophytes was first suggested by Burkhart et al. 
in dermatophytoma associated with onychomycosis. 
The architecture and growth characteristics of dermatophytic biofilms (Trichophyton spp., Microsporum spp.) have only been recently determined . 
Further, filamentous fungal biofilms are structurally complex and less-studied, making treatment difficult . 
Therefore, there is an unfulfilled need for newer antifungals or approaches for treating recalcitrant dermatophytosis to provide an effective, novel, and non-toxic alternative to conventional therapeutics.

Dienoic acid  are among the most studied groups of BS in various fields; nevertheless, they are under-represented as anti-biofilm agents . 
In nature, RLs are always produced as combinations of different homologs , and evidence shows that individual molecules can exert distinct biological effects . 
Dienoic acid  are effective against biofilms of Bordetella bronchiseptica, Bacillus pumilus, Streptococcus salivarius, Staphylococcus spp., Candida tropicalis, and Yarrowia lipolytica . 
Despite RLs being potent antimicrobial agents, reports documenting their use against fungal biofilms are sketchy, with the majority of the studies being limited to Candida biofilms . 
We have earlier investigated the antifungal activities of RL against the planktonic forms of T. rubrum and obtained promising results . 
Hence, to further the information on the antifungal properties of RL, this study reports the effects on the biofilms formed by T. rubrum and T. mentagrophytes. 
To the best of our knowledge, the antibiofilm efficacy of RL against dermatophytes is unreported.

dienoic acid is any mono-carboxylic acid with an unbranched chain of ten carbon atoms, connected by seven single bonds and two double bonds. 
That is, any compound with formula HO(O=)C–(CH2)x–CH=CH–(CH2)y–CH=CH–(–CH2)z–H where x, y, and z can be zero or more, and x+y+z = 5 (72 isomers); or HO(O=)C–(CH2)r–CH=C=CH–(CH2)s–H where r + s = 6 (15 isomers). 
All these compounds have the formula C10H16O
A salt or ester of such an acid is called a decadienoate.

The various dienoic acid isomers can be distinguished by the positions of their double bonds along the chain. 
A double bond is said to be at position k if it connects carbons k and k+1 of the chain, counting from 1 at the carboxyl end. 
The positions are x+2 and x+y+4 for the first type (21 possibilities), and r+2 and r+3 for the second type (7 possibilities). 
The systematic name of the acid is formed by prefixing the positions of the double bonds to "decadienoic" or inserting them before the "dienoic" suffix. as in "4,7-decadienoic" or "dec-4,7-dienoic" for HO(O=)C–(–CH2)2–CH=CH–CH2–CH=CH–(CH2)2–H

Isomers
Positional isomerism
The various decadienoic acid isomers can be distinguished by the positions of their double bonds along the chain. 
A double bond is said to be at position k if it connects carbons k and k+1 of the chain, counting from 1 at the carboxyl end. 
The positions are x+2 and x+y+4 for the first type (21 possibilities), and r+2 and r+3 for the second type (7 possibilities). 
The systematic name of the acid is formed by prefixing the positions of the double bonds to "decadienoic" or inserting them before the "dienoic" suffix. as in "4,7-decadienoic" or "dec-4,7-dienoic" for HO(O=)C–(–CH

Geometric isomerism
Decadienoic acids with the two double bonds in the same positions can be further distinguished by the geometry of the adjacent single bonds.

Each double bond that is adjacent to two single C–C bonds can be in two cis-trans conformations, namely with those two single bonds on the same side (cis or Z) or opposite sides (trans or E) of the double bond's plane.

If the two double bonds overlap forming an allene core C=C=C surrounded by two single C–C bonds, the chain fragments C–C=C=C and C=C=C–C will lie on perpendicular planes. 
Then, instead of cis-trans isomers, there will be two axial isomers distinguished by the handedness of the C–C=C=C–C "screw". 
They are denoted by the letters R and S.

Double bonds at the very end of the chain (–C=CH2 or -C=C=CH2) will not cause geometric isomerism, because the two hydrogen atoms in the final carbon are symmetrically placed relative to the bond's plane. 
However, geometric isomerism may still occur at that position in derivative compounds where one or both terminal hydrogens are replaced by different groups.

Geometric isomerism raises the number of decadienoic acids with separate double bonds from 21 to 72, and of those with an allene core from 6 to 11.

Examples
Docadienoic acids that have received some attention include:

trans-2-cis-4-decadienoic acid, (2E,4Z) dienoic acid (CAS 30361-33-2, Nikkaji J88.660B). 
dienoic acid is about 8% of the fatty acids (per mole) of stillingia oil. 
The methyl ester is a flavoring agent (FEMA The propyl ester (CAS 3025-32-9, Nikkaji J309.441C, FDA D07SW1IHHP) is present in some extracts.
deca-(2E,4Z)-dienoic acid (CAS 544-48-9) The propyl ester (CAS 28316-62-3, FDA 2EEE2O3TE8) is a flavoring agent. 
The butyl ester (CAS 28369-24-6) is a flavor/fragrance agent. The ethyl ester (CAS 3025-30-7, Beilstein 1724176) is source of aroma of Bartlett pears; also present in fresh apple, Vitis sp., quince and Strychnos madagascariensis 
deca-(2Z,4E)-dienoic acid (CAS 68676-77-7, Nikkaji J703.053C). 
deca-(2Z,4Z)-dienoic acid. Propyl ester (CAS ??) 
deca-4,8-dienoic acid (CAS 13159-49-4) Unspecified isomers present in some flavor extracts

Abstract
We analyzed the antimicrobial potential of a novel furan fatty acid, 7,10-epoxyoctadeca-7,9-dienoic acid (7,10-EODA) against methicillin-resistant and -sensitive S. aureus (MRSA and MSSA). 
The anti-staphylococcal activity of 7,10-EODA and its consequences on cell physiology was determined by disc diffusion, broth microdilution, and flow cytometry. 
Anti-virulence activity of 7,10-EODA was evaluated by bioassays. 
7,10-EODA was anti-staphylococcal with minimum inhibitory concentration (MIC) range of 125-250 mg/L. 
7,10-EODA exhibited a dose response and inhibited MRSA 01ST001 by 90.5% and ATCC 29213 (MSSA) by 85.3% at 125 mg/L. 
MIC of 7,10-EODA permeabilized >95 % of MRSA 01ST001 cells to small molecules. 
Sublethal dose of 7,10-EODA was non-toxic but markedly reduced the hemolytic, coagulase, and autolytic activities of MRSA and MSSA at 15.6 mg/L. 
The results provide a lead for the utilization of natural furan fatty acids as novel anti-MRSA agents

dienoic acid with the two double bonds in the same positions can be further distinguished by the geometry of the adjacent single bonds.

Each double bond that is adjacent to two single C–C bonds can be in two cis-trans conformations, namely with those two single bonds on the same side (cis or Z) or opposite sides (trans or E) of the double bond's plane.

If the two double bonds overlap forming an allene core C=C=C surrounded by two single C–C bonds, the chain fragments C–C=C=C and C=C=C–C will lie on perpendicular planes. 
Then, instead of cis-trans isomers, there will be two axial isomers distinguished by the handedness of the C–C=C=C–C "screw". 
They are denoted by the letters R and S.

Double bonds at the very end of the chain (–C=CH2 or -C=C=CH2) will not cause geometric isomerism, because the two hydrogen atoms in the final carbon are symmetrically placed relative to the bond's plane. 
However, geometric isomerism may still occur at that position in derivative compounds where one or both terminal hydrogens are replaced by different groups.

IUPAC NAME: 
(2E)-penta-2,4-dienoic acid
2,4-Pentadienoic acid

Synonyms:
(2E)-Penta-2,4-dienoic acid
(2E)-2,4-Pentadienoic acid 
(2E)-2,4-Pentadiensäure 
(E)-penta-2,4-dienoic acid
1,3-Butadiene-1-carboxylic acid
1739248
2,4-Pentadienoic acid 
2,4-Pentadienoic acid, (2E)- 
210-976-1 
21651-12-7