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505-52-2

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505-52-2 Usage

Chemical Properties

white powder

Uses

1,11-Undecanedicarboxylic Acid is used in the synthesis of two Bis(tetrahydroisoquinoline) which were highly cytotoxic for cancer-cell cultures and less toxic to healthy cells and exhibited noticeable antimicrobial activity against Gram-positive and Gram-negative bacteria and fungal strain Candida albicans.

Definition

ChEBI: An alpha,omega-dicarboxylic acid that is undecane substituted by carboxylic acid groups at positions C-1 and C-11.

Flammability and Explosibility

Nonflammable

Check Digit Verification of cas no

The CAS Registry Mumber 505-52-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,0 and 5 respectively; the second part has 2 digits, 5 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 505-52:
(5*5)+(4*0)+(3*5)+(2*5)+(1*2)=52
52 % 10 = 2
So 505-52-2 is a valid CAS Registry Number.
InChI:InChI=1/C13H24O4/c14-12(15)10-8-6-4-2-1-3-5-7-9-11-13(16)17/h1-11H2,(H,14,15)(H,16,17)/p-2

505-52-2 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (H60962)  Undecane-1,11-dicarboxylic acid, 95%   

  • 505-52-2

  • 1g

  • 120.0CNY

  • Detail
  • Alfa Aesar

  • (H60962)  Undecane-1,11-dicarboxylic acid, 95%   

  • 505-52-2

  • 5g

  • 496.0CNY

  • Detail

505-52-2Synthetic route

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

A

nonanoic acid
112-05-0

nonanoic acid

B

brassylic acid
505-52-2

brassylic acid

Conditions
ConditionsYield
With oxygen; ozone In water; acetone at 0℃; Flow reactor;A 74%
B 88%
2cyclododecanonecarboxylic acid N-phenylamide
37167-18-3

2cyclododecanonecarboxylic acid N-phenylamide

brassylic acid
505-52-2

brassylic acid

Conditions
ConditionsYield
With sodium hydroxide; water In ethanol for 12h; Heating;86%
5,6,7,8,9,10,11,12,13,14-decahydrocyclododeca<1,2-d>pyrimidine(1H,3H)-2,4-dione
63498-96-4

5,6,7,8,9,10,11,12,13,14-decahydrocyclododeca<1,2-d>pyrimidine(1H,3H)-2,4-dione

brassylic acid
505-52-2

brassylic acid

Conditions
ConditionsYield
With potassium hydroxide at 250 - 300℃; for 7h;67%
cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

brassylic acid
505-52-2

brassylic acid

Conditions
ConditionsYield
With dihydrogen peroxide; ortho-tungstic acid In tert-butyl alcohol for 60h; Reflux;53%
With sodium periodate; ruthenium trichloride In water; ethyl acetate; acetonitrile for 2h;52%
With nitric acid
(E,E)-1,5-di-(2-furyl)pent-1,4-dien-3-one
886-77-1

(E,E)-1,5-di-(2-furyl)pent-1,4-dien-3-one

brassylic acid
505-52-2

brassylic acid

Conditions
ConditionsYield
With hydrogenchloride Hydrierung der entstandenen 4.7.10-Trioxotridecandisaeure (als Natriumsalz) an einem Nickelkatalysator in Wasser bei 200grad und 130 at Druck;
Brassidic acid
506-33-2

Brassidic acid

brassylic acid
505-52-2

brassylic acid

Conditions
ConditionsYield
With chloroform; ozone
With ozone; acetic acid
1,9-Dibromononane
4549-33-1

1,9-Dibromononane

sodium diethylmalonate
996-82-7

sodium diethylmalonate

brassylic acid
505-52-2

brassylic acid

Conditions
ConditionsYield
With ethanol at 125℃; Beim Verseifung und Erhitzen der Tetracarbonsaeure auf 180grad;
With ethanol Beim Verseifung und Erhitzen der Tetracarbonsaeure auf 180grad;
tridecanedinitrile
6006-37-7

tridecanedinitrile

brassylic acid
505-52-2

brassylic acid

Conditions
ConditionsYield
With potassium hydroxide
With hydrogenchloride at 120℃;
11-bromoundecanoic acid
2834-05-1

11-bromoundecanoic acid

sodium diethylmalonate
996-82-7

sodium diethylmalonate

brassylic acid
505-52-2

brassylic acid

Conditions
ConditionsYield
With ethanol Erwaermen des Reaktionsprodukts mit wss.Kalilauge und Erhitzen der erhaltenen Saeure auf 170grad;
11-bromo-undecanoic acid methyl ester
6287-90-7

11-bromo-undecanoic acid methyl ester

sodium diethylmalonate
996-82-7

sodium diethylmalonate

brassylic acid
505-52-2

brassylic acid

Conditions
ConditionsYield
und Verseifen des entstehenden Undecantricarbonsaeureesters mit alkoholischer Kalilauge zur freie Saeure und Erhitzen diese auf ca.114grad;
13-oxotetradecanoic acid
2389-02-8

13-oxotetradecanoic acid

brassylic acid
505-52-2

brassylic acid

Conditions
ConditionsYield
With sodium hypobromide
behenolic acid
506-35-4

behenolic acid

brassylic acid
505-52-2

brassylic acid

Conditions
ConditionsYield
With nitric acid
7-oxotridecanoic acid
92155-72-1

7-oxotridecanoic acid

brassylic acid
505-52-2

brassylic acid

Conditions
ConditionsYield
With sodium hydroxide; hydrazine hydrate; diethylene glycol at 195℃;
13-cyclopent-2-enyl-tridecanoic acid
502-30-7

13-cyclopent-2-enyl-tridecanoic acid

brassylic acid
505-52-2

brassylic acid

Conditions
ConditionsYield
With permanganate(VII) ion
2,2'-methylenebis(cyclohexane-1,3-dione)
54135-60-3

2,2'-methylenebis(cyclohexane-1,3-dione)

brassylic acid
505-52-2

brassylic acid

Conditions
ConditionsYield
With sodium hydroxide; hydrazine hydrate; diethylene glycol at 125℃; Reagens 4:Methanol; anschliessenden Erhitzen auf 195grad;
cyclotridecanone
832-10-0

cyclotridecanone

brassylic acid
505-52-2

brassylic acid

Conditions
ConditionsYield
With chromium(VI) oxide; acetic acid
13-hydroxytridecanoic acid
7735-38-8

13-hydroxytridecanoic acid

brassylic acid
505-52-2

brassylic acid

Conditions
ConditionsYield
With nitric acid
13-(2-furyl)-tridec-1-yne
24708-33-6

13-(2-furyl)-tridec-1-yne

brassylic acid
505-52-2

brassylic acid

Conditions
ConditionsYield
(i) O3, EtOAc, AcOH, (ii) H2O, H2O2; Multistep reaction;
10-undecenoic acid
112-38-9

10-undecenoic acid

methanetricarboxylic acid triethyl ester
6279-86-3

methanetricarboxylic acid triethyl ester

brassylic acid
505-52-2

brassylic acid

Conditions
ConditionsYield
With di-tert-butyl peroxide
undecane-1,1,11-tricarboxylic acid
53227-26-2

undecane-1,1,11-tricarboxylic acid

brassylic acid
505-52-2

brassylic acid

Conditions
ConditionsYield
(i) aq. H2SO4, (ii) undecane, (heating); Multistep reaction;
undecane-1,1,11-tricarboxylic acid-1,1-diethyl ester-11-methyl ester
22623-84-3

undecane-1,1,11-tricarboxylic acid-1,1-diethyl ester-11-methyl ester

brassylic acid
505-52-2

brassylic acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol Heating;
3,9-Dioxo-undecan-dicarbonsaeure-(1,11)
4297-19-2

3,9-Dioxo-undecan-dicarbonsaeure-(1,11)

brassylic acid
505-52-2

brassylic acid

Conditions
ConditionsYield
With sodium hydroxide; hydrazine hydrate In diethylene glycol at 200 - 220℃;
1,2-Cyclotetradecadien
14108-91-9

1,2-Cyclotetradecadien

brassylic acid
505-52-2

brassylic acid

Conditions
ConditionsYield
(i) O3, (ii) AcOOH; Multistep reaction;
1,5-Diazacyclooctadecan-6,18-dion
139662-49-0

1,5-Diazacyclooctadecan-6,18-dion

A

brassylic acid
505-52-2

brassylic acid

B

1,3-diaminopropane dihydrochloride
10517-44-9

1,3-diaminopropane dihydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water at 150℃;
1,6-Diazacyclononadecan-7,19-dion
139662-50-3

1,6-Diazacyclononadecan-7,19-dion

A

brassylic acid
505-52-2

brassylic acid

B

putrescine dihydrochloride
333-93-7

putrescine dihydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water at 150℃;
2-oxo-cyclododecane-1-carbonitrile
66819-72-5

2-oxo-cyclododecane-1-carbonitrile

brassylic acid
505-52-2

brassylic acid

Conditions
ConditionsYield
With hydrogenchloride; potassium hydroxide 1.) H2O, ethanol, reflux, 8 h; Yield given. Multistep reaction;
μ.ν-dioxy-behenic acid

μ.ν-dioxy-behenic acid

brassylic acid
505-52-2

brassylic acid

Conditions
ConditionsYield
With potassium hydroxide; potassium chlorate at 200 - 220℃;
12-hydroxy-dodecane-carboxylic acid-(1)

12-hydroxy-dodecane-carboxylic acid-(1)

brassylic acid
505-52-2

brassylic acid

Conditions
ConditionsYield
With chromic acid; acetic acid
pelargonylbrassylamic acid

pelargonylbrassylamic acid

brassylic acid
505-52-2

brassylic acid

Conditions
ConditionsYield
With hydrogenchloride at 150℃;
vinyl propionate
105-38-4

vinyl propionate

brassylic acid
505-52-2

brassylic acid

divinyl tridecanedioate
15423-11-7

divinyl tridecanedioate

Conditions
ConditionsYield
With sulfuric acid; mercury(II) diacetate at 20 - 50℃; for 4h;100%
With sulfuric acid; mercury(II) diacetate
triethylsilane
617-86-7

triethylsilane

brassylic acid
505-52-2

brassylic acid

C37H84O4Si4

C37H84O4Si4

Conditions
ConditionsYield
With decacarbonyldirhenium(0) In toluene at 20℃; for 9h; Concentration; Schlenk technique; Inert atmosphere; UV-irradiation;99%
With dimanganese decacarbonyl In toluene at 20℃; for 3h; Inert atmosphere; Irradiation;97%
brassylic acid
505-52-2

brassylic acid

2,3-Epoxypropyl methacrylate
106-91-2

2,3-Epoxypropyl methacrylate

bis[methacryloyloxy-2-hydroxy-propyl] tridecanedioate

bis[methacryloyloxy-2-hydroxy-propyl] tridecanedioate

Conditions
ConditionsYield
With triphenylphosphine at 90℃; for 3h;99%
methanol
67-56-1

methanol

brassylic acid
505-52-2

brassylic acid

dimethyl 1,11-undecanedicarboxylate
1472-87-3

dimethyl 1,11-undecanedicarboxylate

Conditions
ConditionsYield
With sulfuric acid for 5h; Heating;98%
With sulfuric acid for 2h; Reflux;91%
With thionyl chloride65%
brassylic acid
505-52-2

brassylic acid

1,13-tridecanediol
13362-52-2

1,13-tridecanediol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 5.5h; Reflux;97%
With zirconium(IV) borohydride In tetrahydrofuran at 25℃; for 1h; Reduction;95%
With lithium aluminium tetrahydride In tetrahydrofuran for 2h; Ambient temperature;93%
1,6-Hexanediamine
124-09-4

1,6-Hexanediamine

brassylic acid
505-52-2

brassylic acid

1,6-hexamethylene diamine brassylic acid
54545-73-2

1,6-hexamethylene diamine brassylic acid

Conditions
ConditionsYield
In ethanol at 50 - 80℃; for 2h;96%
brassylic acid
505-52-2

brassylic acid

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

N1,N13-bis(3,4-dimethoxy-β-phenylethyl)brassyldiamide

N1,N13-bis(3,4-dimethoxy-β-phenylethyl)brassyldiamide

Conditions
ConditionsYield
In methanol at 178℃; for 2h;91%
brassylic acid
505-52-2

brassylic acid

tridecanedioyl dichloride
35691-43-1

tridecanedioyl dichloride

Conditions
ConditionsYield
With thionyl chloride In dichloromethane Heating;90%
With thionyl chloride
With thionyl chloride for 3h; Heating;
brassylic acid
505-52-2

brassylic acid

3β-hydroxy-14β,16β-O-(4-methoxybenzylidene)card-20(22)-enolide
190579-30-7

3β-hydroxy-14β,16β-O-(4-methoxybenzylidene)card-20(22)-enolide

hydrogen 14β,16β-O-(4-methoxybenzylidene)card-20(22)-enolide-3β-yl 1,11-undecanedicarboxylate
190579-39-6

hydrogen 14β,16β-O-(4-methoxybenzylidene)card-20(22)-enolide-3β-yl 1,11-undecanedicarboxylate

Conditions
ConditionsYield
With pyridine; p-toluenesulfonyl chloride for 4h; Ambient temperature;88%
brassylic acid
505-52-2

brassylic acid

((3S,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diyl)dimethanamine
1309611-91-3

((3S,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diyl)dimethanamine

isoidide-2,5-dimethylamine brassylic acid
1414371-76-8

isoidide-2,5-dimethylamine brassylic acid

Conditions
ConditionsYield
In ethanol; water at 50 - 80℃; for 2h;81%
brassylic acid
505-52-2

brassylic acid

[(1-methoxy-2-methyl-1-butenyl)oxy]trimethylsilane
123820-43-9, 123820-44-0, 84393-12-4

[(1-methoxy-2-methyl-1-butenyl)oxy]trimethylsilane

dimethyl 2,16-diethyl-2,16-dimethyl-3,15-dioxoheptadecanedioate

dimethyl 2,16-diethyl-2,16-dimethyl-3,15-dioxoheptadecanedioate

Conditions
ConditionsYield
Stage #1: brassylic acid With 2,4-Dichlorobenzenesulfonyl chloride; triethylamine In dichloromethane at 0 - 5℃; for 1h;
Stage #2: [(1-methoxy-2-methyl-1-butenyl)oxy]trimethylsilane With dmap; titanium tetrachloride In dichloromethane at 20 - 25℃; for 1.5h; Claisen condensation;
71%
brassylic acid
505-52-2

brassylic acid

C21H25N7O

C21H25N7O

C55H70N14O4*6ClH

C55H70N14O4*6ClH

Conditions
ConditionsYield
Stage #1: C21H25N7O With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.166667h; Cooling;
Stage #2: brassylic acid In N,N-dimethyl-formamide for 0.166667h; Further stages;
70%
1-methoxy-2-methyl-1-trimethylsiloxy-1-propene
31469-15-5

1-methoxy-2-methyl-1-trimethylsiloxy-1-propene

brassylic acid
505-52-2

brassylic acid

dimethyl 2,2,16,16-tetramethyl-3,15-dioxoheptadecanedioate

dimethyl 2,2,16,16-tetramethyl-3,15-dioxoheptadecanedioate

Conditions
ConditionsYield
Stage #1: brassylic acid With 2,4-Dichlorobenzenesulfonyl chloride; triethylamine In dichloromethane at 0 - 5℃; for 1h;
Stage #2: 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene With dmap; titanium tetrachloride In dichloromethane at 20 - 25℃; for 1.5h; Claisen condensation;
69%
brassylic acid
505-52-2

brassylic acid

3,4-methylenedioxyphenylethylamine
1484-85-1

3,4-methylenedioxyphenylethylamine

N1,N13-bis(3,4-methylenedioxy-β-phenylethyl)brassyldiamide

N1,N13-bis(3,4-methylenedioxy-β-phenylethyl)brassyldiamide

Conditions
ConditionsYield
In methanol at 178℃; for 2h;69%
brassylic acid
505-52-2

brassylic acid

C20-O-trityl-prostratin-ol
1262389-74-1

C20-O-trityl-prostratin-ol

C52H64O8

C52H64O8

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 19h;57.84%
brassylic acid
505-52-2

brassylic acid

7-Oxocholesterol
566-28-9

7-Oxocholesterol

13-oxo-13-(7-ketocholest-5-en-3β-yloxy)tridecanoic acid

13-oxo-13-(7-ketocholest-5-en-3β-yloxy)tridecanoic acid

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetone at 20℃; for 48h; Purification / work up;56%
brassylic acid
505-52-2

brassylic acid

benzyl bromide
100-39-0

benzyl bromide

A

Dibenzyl-brassylat
52175-11-8

Dibenzyl-brassylat

B

13-benzyloxy-13-oxotridecanoic acid
261178-55-6

13-benzyloxy-13-oxotridecanoic acid

Conditions
ConditionsYield
With potassium hydroxide; tetrabutylammomium bromide In tetrahydrofuran; methanol for 6h; Alkylation; Thermolysis;A 22%
B 52%
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

uranyl nirate hexahydrate

uranyl nirate hexahydrate

brassylic acid
505-52-2

brassylic acid

C10H8N2*C13H22O4(2-)*O2U(2+)

C10H8N2*C13H22O4(2-)*O2U(2+)

Conditions
ConditionsYield
With manganese (II) nitrate tetrahydrate In 1-methyl-pyrrolidin-2-one; water at 140℃; for 168h;51%
1,10-Phenanthroline
66-71-7

1,10-Phenanthroline

uranyl nirate hexahydrate

uranyl nirate hexahydrate

brassylic acid
505-52-2

brassylic acid

C13H22O4(2-)*C12H8N2*O2U(2+)

C13H22O4(2-)*C12H8N2*O2U(2+)

Conditions
ConditionsYield
With manganese (II) nitrate tetrahydrate In 1-methyl-pyrrolidin-2-one; water at 140℃;47%
brassylic acid
505-52-2

brassylic acid

benzyl bromide
100-39-0

benzyl bromide

13-benzyloxy-13-oxotridecanoic acid
261178-55-6

13-benzyloxy-13-oxotridecanoic acid

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran; hexane; water; ethyl acetate at 0 - 20℃;46%
brassylic acid
505-52-2

brassylic acid

template CS diol
110224-49-2

template CS diol

C64H68O4
110224-58-3

C64H68O4

Conditions
ConditionsYield
With dmap; 4-(dimethylamino)pyridine hydrochloride; dicyclohexyl-carbodiimide In chloroform for 14h; Heating;43%
brassylic acid
505-52-2

brassylic acid

2-(4-(3-isopropyl-2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-1H-indol-5-yl)piperidin-1-yl)ethan-1-amine

2-(4-(3-isopropyl-2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-1H-indol-5-yl)piperidin-1-yl)ethan-1-amine

N1,N13-bis(2-(4-(3-isopropyl-2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-1H-indol-5-yl)piperidin-1-yl)ethyl)tridecanediamide

N1,N13-bis(2-(4-(3-isopropyl-2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-1H-indol-5-yl)piperidin-1-yl)ethyl)tridecanediamide

Conditions
ConditionsYield
Stage #1: brassylic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide for 0.5h;
Stage #2: 2-(4-(3-isopropyl-2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-1H-indol-5-yl)piperidin-1-yl)ethan-1-amine In N,N-dimethyl-formamide for 1h;
40.8%
brassylic acid
505-52-2

brassylic acid

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

12-(1,4-Naphthochinon-2-yl)dodecansaeure
132080-50-3

12-(1,4-Naphthochinon-2-yl)dodecansaeure

Conditions
ConditionsYield
With ammonium peroxydisulfate; silver nitrate In water; acetonitrile for 0.166667h; Heating;38%
2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin
14098-44-3

2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin

brassylic acid
505-52-2

brassylic acid

1,13-Bis-(6,7,9,10,12,13,15,16-octahydro-5,8,11,14,17-pentaoxa-benzocyclopentadecen-2-yl)-tridecane-1,13-dione
135442-41-0

1,13-Bis-(6,7,9,10,12,13,15,16-octahydro-5,8,11,14,17-pentaoxa-benzocyclopentadecen-2-yl)-tridecane-1,13-dione

Conditions
ConditionsYield
With PPA; Polyphosphoric acid (PPA) at 85 - 90℃; for 7h;31%
brassylic acid
505-52-2

brassylic acid

4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl
14691-88-4

4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

C22H41N2O4
82032-31-3

C22H41N2O4

Conditions
ConditionsYield
With 4-dimethylpyridine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide 1.) 0 degC 45 min., 2.) R.T. 48 h;26%
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
14098-24-9

2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin

brassylic acid
505-52-2

brassylic acid

1,13-Bis-(6,7,9,10,12,13,15,16,18,19-decahydro-5,8,11,14,17,20-hexaoxa-benzocyclooctadecen-2-yl)-tridecane-1,13-dione
135442-44-3

1,13-Bis-(6,7,9,10,12,13,15,16,18,19-decahydro-5,8,11,14,17,20-hexaoxa-benzocyclooctadecen-2-yl)-tridecane-1,13-dione

Conditions
ConditionsYield
With PPA; Polyphosphoric acid (PPA) at 85 - 90℃; for 7h;22%

505-52-2Relevant articles and documents

Mitwa et al.

, p. 159 (1968)

Dudinov et al.

, (1974)

Process for producing long chain amino acids and dibasic acids

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, (2018/09/21)

There is disclosed a process for the production of long chain amino acid and long chain dibasic acid, comprising: (1) reacting long chain keto fatty acid with hydroxylamine or subjecting keto fatty acid to an ammoximation reaction to yield an oxime fatty acid; (2) subjecting the oxime fatty acid to the Beckmann rearrangement to yield a mixture of two amide fatty acids; (3) hydrolyzing the mixed amide fatty acids to produce long chain amino acid, long chain dibasic acid, short chain alkylamine, and alkanoic acid.

Production of Odd-Carbon Dicarboxylic Acids in Escherichia coli Using an Engineered Biotin-Fatty Acid Biosynthetic Pathway

Haushalter, Robert W.,Phelan, Ryan M.,Hoh, Kristina M.,Su, Cindy,Wang, George,Baidoo, Edward E. K.,Keasling, Jay D.

supporting information, p. 4615 - 4618 (2017/04/11)

Dicarboxylic acids are commodity chemicals used in the production of plastics, polyesters, nylons, fragrances, and medications. Bio-based routes to dicarboxylic acids are gaining attention due to environmental concerns about petroleum-based production of these compounds. Some industrial applications require dicarboxylic acids with specific carbon chain lengths, including odd-carbon species. Biosynthetic pathways involving cytochrome P450-catalyzed oxidation of fatty acids in yeast and bacteria have been reported, but these systems produce almost exclusively even-carbon species. Here we report a novel pathway to odd-carbon dicarboxylic acids directly from glucose in Escherichia coli by employing an engineered pathway combining enzymes from biotin and fatty acid synthesis. Optimization of the pathway will lead to industrial strains for the production of valuable odd-carbon diacids.

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