693-23-2

Basic information

• Product Name: Dodecanedioic acid
• Synonyms: DODECANEDIOIC ACID FOR SYNTHESIS;Dodecanedioic aci;Twelve alkyl acid;1.10-Decanedic;Dodecandioic acid (DDA);1,10-decandicarboxylicacid;1,10-dicarboxydecane;DECAMETHYLENEDICARBOXYLIC ACID
• CAS NO: 693-23-2
• Molecular Formula: C₁₂H₂₂O₄
• Molecular Weight: 230.3
• EINECS: 211-746-3
• Product Categories: Dicarboxylic Acids;Fatty Acids and conjugates;Fatty Acyls;Lipids;Organic Building Blocks;Dodecanedioic acid;Industrial/Fine Chemicals;alpha,omega-Alkanedicarboxylic Acids;alpha,omega-Bifunctional Alkanes;Monofunctional & alpha,omega-Bifunctional Alkanes;Aliphatics;Fatty Acid Derivatives & Lipids;Glycerols;Biochemicals and Reagents;Building Blocks;C11 to C12;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis
• Mol File: 693-23-2.mol
• Article Data: 64

Chemical Properties

• Melting Point: 127-129 °C(lit.)
• Boiling Point: 245 °C10 mm Hg(lit.)
• Flash Point: 220 °C
• Appearance: White/Pellets or Powder
• Density: 1,15 g/cm3
• Vapor Pressure: 21 mm Hg ( 222 °C)
• Refractive Index: 1.4437 (estimate)
• Storage Temp.: −20°C
• Solubility: ethanol: 0.1 g/mL, clear
• PKA: 4.48±0.10(Predicted)
• Water Solubility: < 0.1 g/L (20℃)
• Sensitive: Air Sensitive
• Stability: Stable. Incompatible with strong oxidizing agents, reducing agents. Combustible.
• BRN: 1782580
• CAS DataBase Reference: Dodecanedioic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Dodecanedioic acid(693-23-2)
• EPA Substance Registry System: Dodecanedioic acid(693-23-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36
• Safety Statements: 26-36-24/25
• RTECS: JR2370000
• TSCA: Yes
• Hazardous Substances Data: 693-23-2(Hazardous Substances Data)

Usage

Description

This acid is used in the production of nylon (nylon - 6,12), polyamides, coatings, adhesives, greases, polyesters, dyestuffs, detergents, flame retardants, and fragrances. It is now produced by fermentation of long-chain alkanes with a specific strain of Candida tropicalis. Its monounsaturated analogue (traumatic acid) is described below.

Chemical Properties

white crystalline powder

Uses

Different sources of media describe the Uses of 693-23-2 differently. You can refer to the following data:
1. Induced mutation of dodecanedioic acid producing Candida tropicalis.
2. Dodecanedioic acid is used as an intermediate for plasticizers, lubricants and adhesives. It is also used in antiseptics, top-grade coatings, painting materials, corrosion inhibitor and surfactant. It finds application in engineering plastics such as nylon 612.

Preparation

Dodecanedioic acid is prepared from cyc1ododecene (obtained from butadiene) by methods which are entirely analogous to those used to prepare adipic acid from benzene. The cyclododecene is reduced to cyclododecane, which is oxidized firstly to a mixture of cyc1ododecanol and cyclododecanone and then to dodecanedioic acid. Dodecanedioic acid is a colourless crystalline solid, m.p. 129°C.

Definition

ChEBI: An alpha,omega-dicarboxylic acid that is dodecane in which the methyl groups have been oxidised to the corresponding carboxylic acids.

Purification Methods

Crystallise the dioic acid from water, 75% or 95% EtOH (solubility is 10%), or glacial acetic acid. [Beilstein 2 IV 2126.]

InChI:InChI=1/C12H22O4/c13-11(14)9-7-5-3-1-2-4-6-8-10-12(15)16/h1-10H2,(H,13,14)(H,15,16)/p-2

Synthetic route

1,12-dodecandiol (5675-51-4) → 1,12-dodecanedioic acid (693-23-2)

Conditions	Yield
With air; sodium nitrite In trifluoroacetic acid at 0 - 20℃; for 5h;	100%
With hydrogenchloride; calcium hypochlorite In tetrachloromethane; tert-butyl alcohol for 7h;	58%

11-cyanoundecanoic acid methyl ester (22915-49-7) → 1,12-dodecanedioic acid (693-23-2)

Conditions	Yield
With hydrogenchloride; water for 2.5h; Reflux;	100%

2-nitrocyclododecanone (95338-32-2, 13154-31-9) → 1,12-dodecanedioic acid (693-23-2)

Conditions	Yield
With dihydrogen peroxide; potassium carbonate In methanol for 10h; Ambient temperature;	92%
With Oxone; sodium hydroxide; disodium hydrogenphosphate; water 1.) MeOH, 70 deg C, 4 h, 2.) MeOH, r.t., 4 h; Yield given. Multistep reaction;

1,3-Dioxa-cyclopentadecane-4,15-dione → 12-hydroxydodecanoic acid (505-95-3) + 1,12-dodecandiol (5675-51-4) + 1,12-dodecanedioic acid (693-23-2)

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran at 65℃; for 6h;	A 85% B 8% C 6%
With sodium tetrahydroborate In tetrahydrofuran at 23℃; for 120h;	A 82% B 12% C n/a
With sodium tetrahydroborate In tetrahydrofuran at 65℃; for 9h; Product distribution; influence of temperature, reaction time;	A 77% B 11% C 9%
With sodium tetrahydroborate In tetrahydrofuran at 65℃; for 6h;	A 66% B 6% C 11%

cyclododecene (1501-82-2) → 1,12-dodecanedioic acid (693-23-2)

Conditions	Yield
With Oxone; 2-iodo-3,4,5,6-tetramethylbenzoic acid In water; acetonitrile for 24h;	85%
With tetrafluoroboric acid; iodomesitylene; 3-chloro-benzenecarboperoxoic acid In dichloromethane; water; acetonitrile at 50℃; for 10h; Inert atmosphere;	77 %Spectr.
With potassium peroxymonosulfate; iodobenzene In water; acetonitrile at 60℃; for 8h;	82 %Spectr.

(1S,2S)-Cyclododecane-1,2-diol (118101-31-8) → 1,12-dodecanedioic acid (693-23-2)

Conditions	Yield
With potassium carbonate; stearic acid at 50℃; for 22.5h; electrolysis: nickel(III) oxide hydroxide electrode, 0.3 A;	84%

dec-1-en-3-ol (74824-56-9, 74867-43-9, 74867-44-0, 51100-54-0) + carbon monoxide (201230-82-2) → 1,12-dodecanedioic acid (693-23-2)

Conditions	Yield
With HeMaRaphos; water; toluene-4-sulfonic acid; palladium dichloride In tetrahydrofuran at 125℃; under 30003 Torr; for 24h; Autoclave; Green chemistry; regioselective reaction;	83%

cyclododecanol (1724-39-6) → 1,12-dodecanedioic acid (693-23-2) + cyclododecanone (830-13-7)

Conditions	Yield
With oxygen; sodium nitrite In trifluoroacetic acid at 0 - 20℃; for 5h;	A 80% B 10%

1,12-dimethoxydodecane (73120-52-2) → 1,12-dodecanedioic acid (693-23-2)

Conditions	Yield
With lithium nitrate In water; acetonitrile at 25℃; anodic oxidation;	78%

cyclododecanone (830-13-7) → oxacyclotridecan-2-one (947-05-7) + 12-hydroxydodecanoic acid (505-95-3) + 1,12-dodecanedioic acid (693-23-2)

Conditions	Yield
With maleic anhydride; dihydrogen peroxide In dichloromethane; acetic anhydride for 15h; Heating;	A 77% B n/a C n/a

cis-1,2-cyclododecanediol (4422-05-3) → 12-oxododecanoic acid (3956-80-7) + 1,12-dodecanedioic acid (693-23-2) + dodecanedial (38279-34-4) + cyclododecane-1,2-dione (3008-41-1)

Conditions	Yield
With Oxone; sodium ortho-iodobenzenesulfonate In acetonitrile at 70℃; for 1h;	A n/a B n/a C n/a D 72%

cyclododecane (294-62-2) → 1,12-dodecanedioic acid (693-23-2)

Conditions	Yield
With N-hydroxyphthalimide; bis(acetylacetonato)manganese(II); oxygen; acetic acid at 70℃; under 760.051 Torr; for 14h;	68%

cyclohexanone (108-94-1) → 1,12-dodecanedioic acid (693-23-2)

Conditions	Yield
Stage #1: cyclohexanone With dihydrogen peroxide In water at 25 - 30℃; for 0.25h; UV-irradiation; Stage #2: In water at 50℃; for 6h; Temperature; UV-irradiation;	67.1%
Multi-step reaction with 2 steps 1: H2O2; water 2: iron (II)-sulfate; aqueous sulfuric acid View Scheme
Multi-step reaction with 2 steps 1: H2O2; diethyl ether 2: iron (II)-sulfate heptahydrate; methanol View Scheme

12-hydroxydodecanoic acid (505-95-3) → 1,12-dodecanedioic acid (693-23-2)

Conditions	Yield
With hydrogenchloride; calcium hypochlorite In tetrachloromethane; tert-butyl alcohol for 7h;	65%
With oleate hydratase from S. maltophilia In aq. buffer at 35℃; for 2h; pH=8; Enzymatic reaction;	46%
With chromium(VI) oxide; acetic acid

(E)-Cyclododecen (1486-75-5) → 1,12-dodecanedioic acid (693-23-2)

Conditions	Yield
With jones reagent; osmium(VIII) oxide In water; acetone for 20h; Ambient temperature;	65%

C48H88O16 (74515-85-8) → ethene (74-85-1) + 1,12-dodecanedioic acid (693-23-2) + 12-oxo-tetradecanoic acid (2177-96-0) + carbon monooxide, carbon dioxide, oxygen

Conditions	Yield
In n-heptane at 100℃; Product distribution; var. solvent, var. temp.;	A n/a B 60% C 12% D n/a

cyclododecane-1,2-dione (3008-41-1) → 1,12-dodecanedioic acid (693-23-2)

Conditions	Yield
With dihydrogen peroxide In methanol; water for 2h; Ambient temperature;	47%

oligomeric diacyl peroxide → 1,12-dodecanedioic acid (693-23-2)

Conditions	Yield
With potassium hydroxide for 48h;	47%

1,12-Diaminododecane (2783-17-7) → 1,12-dodecanedioic acid (693-23-2)

Conditions	Yield
Pseudomonas K24	7%

2-Acetoxycyclododecanone (26307-31-3) → 1,12-dodecanedioic acid (693-23-2) + 2-hydroxycyclododecanone (19025-38-8, 140134-30-1)

Conditions	Yield
With potassium hydroxide In methanol	A 4.9 g B 3.1%
With potassium hydroxide In methanol Heating;	A 4.9 g B 3.1 g

1,5-dibromo-pentane (111-24-0) → 1,12-dodecanedioic acid (693-23-2)

Conditions	Yield
With diethyl ether; magnesium bei der Einw. von Kohlendioxid auf das Reaktionsprodukt;

1-hydroxycyclohexyl 1-hydroperoxycyclohexyl peroxide (78-18-2) → 1,12-dodecanedioic acid (693-23-2)

Conditions	Yield
With sulfuric acid; iron(II) sulfate
With methanol; iron(II) sulfate

1-hydroxycyclohexyl 1-hydroperoxycyclohexyl peroxide (78-18-2) → Adipic acid (124-04-9) + 1,12-dodecanedioic acid (693-23-2) + cyclohexanone (108-94-1) + hexanoic acid (142-62-1)

Conditions	Yield
at 110 - 160℃;

dodec-6c-enedioic acid (55311-11-0) → 1,12-dodecanedioic acid (693-23-2)

Conditions	Yield
With 1,4-dioxane; platinum Hydrogenation;

12-Hydroxystearic acid (106-14-9) → azelaic acid (123-99-9) + 1,12-dodecanedioic acid (693-23-2)

Conditions	Yield
With nitric acid
With ammonium vanadate bei Siedetemperatur;
With nitric acid

12-Hydroxystearic acid (106-14-9) → undecanedioic acid (1852-04-6) + 1,12-dodecanedioic acid (693-23-2)

Conditions	Yield
With nitric acid
With ammonium vanadate; nitric acid
With nitric acid

12-Hydroxystearic acid (106-14-9) → 1,12-dodecanedioic acid (693-23-2)

Conditions	Yield
With potassium hydroxide; sodium hydroxide; paraffin oil at 320℃;

1,8-diiodooctane (24772-63-2) + sodium diethylmalonate (996-82-7) → 1,12-dodecanedioic acid (693-23-2)

Conditions	Yield
With ethanol Erwaermen des Reaktionsgemisches mit wss.Natronlauge und Erhitzen des nach dem Ansaeuern erhaltenen Reaktionsprodukts auf 180grad;

1,12-dodecanedinitrile (4543-66-2) → 1,12-dodecanedioic acid (693-23-2)

Conditions	Yield
With sodium ethanolate

1,12-dodecanedioic acid (693-23-2) → 1,12-dodecanedioyl dichloride (4834-98-4)

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide for 2h; Reflux;	100%
With thionyl chloride Heating;	95%
With thionyl chloride

methanol (67-56-1) + 1,12-dodecanedioic acid (693-23-2) → dodecanedioic acid dimethyl ester (1731-79-9)

Conditions	Yield
With boron trifluoride at 65℃; for 0.333333h;	100%
With sulfuric acid for 24h; Reflux; Inert atmosphere;	100%
With sulfuric acid Heating;	99%

1,12-dodecanedioic acid (693-23-2) + 1,1'-carbonyldiimidazole (530-62-1) → 1,12-Di-imidazol-1-yl-dodecane-1,12-dione (122236-61-7)

Conditions	Yield
In neat (no solvent) for 2h;	100%
In N,N-dimethyl acetamide at 40℃;
In tetrahydrofuran for 24h; Ambient temperature;
In tetrahydrofuran

di(succinimido) carbonate (74124-79-1) + 1,12-dodecanedioic acid (693-23-2) → dodecanedioic acid bis(2,5-dioxopyrrolidin-1-yl) ester (75472-90-1)

Conditions	Yield
With pyridine In acetonitrile at 20℃; for 7h;	100%
With pyridine In acetonitrile at 20℃; for 7h; Inert atmosphere;	100%
With pyridine In acetonitrile at 20℃; for 3h;	90%

vinyl propionate (105-38-4) + 1,12-dodecanedioic acid (693-23-2) → dodecandioic acid divinyl ester

Conditions	Yield
With sulfuric acid; mercury(II) diacetate at 20 - 50℃; for 4h;	100%
With sulfuric acid; mercury(II) diacetate

1,12-dodecanedioic acid (693-23-2) → dodecanedial (38279-34-4)

Conditions	Yield
With 9-borabicyclo[3.3.1]nonane dimer; lithium dihydrido borata-bicyclo[3.3.0]nonane In tetrahydrofuran for 1h; Ambient temperature;	99%
With hydrogen; 2,2-dimethylpropanoic anhydride; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 80℃; under 22501.8 Torr; for 24h;	75%
With thexylchloroborane*methyl sulfide In dichloromethane for 0.25h; Ambient temperature;

1-octadecanol (112-92-5) + 1,12-dodecanedioic acid (693-23-2) → distearyl dodecanedioate (42234-06-0)

Conditions	Yield
With 1-hexadecyl-3-sulfo-1H-imidazol-3-ium chloride In neat (no solvent) at 110℃; for 16h; Green chemistry;	99%

ethanol (64-17-5) + 1,12-dodecanedioic acid (693-23-2) → diethyl dodecanedioate (10471-28-0)

Conditions	Yield
for 2h; Reflux; Acidic conditions;	98%
With sulfuric acid for 2h; Reflux;	98%
With hydrogenchloride decane-dicarboxylic acid-(1.10)-di--ester;

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 1,12-dodecanedioic acid (693-23-2) → dodecanedioic acid bis(2,5-dioxopyrrolidin-1-yl) ester (75472-90-1)

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 24h;	98%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; dimethyl sulfoxide at 20℃;

1,12-dodecanedioic acid (693-23-2) + tetramethyl ammoniumhydroxide (75-59-2) → bis(tetramethylammonium) dodecanedioate

Conditions	Yield
In methanol at 21℃; for 48h;	98%

1,12-dodecanedioic acid (693-23-2) + 2,3-Epoxypropyl methacrylate (106-91-2) → 1,12-bis[2-hydroxy-3-methacryloyloxypropyl] dodecanedioate

Conditions	Yield
With triphenylphosphine at 90℃; for 3h;	98%

1,12-dodecanedioic acid (693-23-2) → 1,12-dodecandiol (5675-51-4)

Conditions	Yield
With tricarbonyl(η(4)-cycloocta-1,5-diene)iron; phenylsilane In tetrahydrofuran at 20℃; for 24h; UV-irradiation; Inert atmosphere; chemoselective reaction;	97%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃;	91%
Multi-step reaction with 2 steps 1: sulfuric acid / Heating 2: LiAlH4 / diethyl ether / 0 °C View Scheme
Stage #1: 1,12-dodecanedioic acid With 4-methyl-morpholine; chloroformic acid ethyl ester In tetrahydrofuran at 2℃; for 0.25h; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water at 2℃;

1,12-dodecanedioic acid (693-23-2) + isobutene (115-11-7) → 1,10-decanedicarboxylic acid mono-tert-butyl ester (234081-98-2)

Conditions	Yield
With graphene-ferric oxide composite nanomaterial In dichloromethane for 4h; Solvent; Reagent/catalyst; Cooling with ice;	95.3%
With graphene/ferric oxide composite nanomaterial In dichloromethane; di-isopropyl ether for 4h; Solvent; Cooling with ice;

imidazolidone (120-93-4) + 1,12-dodecanedioic acid (693-23-2) → poly[N,N-(1,10-decanedicarboxyl)-2-imidazolidone], Mw 22000, Mn 8100, DP 34; monomer(s): 1,10-decanedicarboxylic acid; 2-imidazolidone

Conditions	Yield
With 3,5-bis-trifluromethylphenylboronic acid In 1,3,5-trimethyl-benzene for 24h; Heating;	95%

1,12-dodecanedioic acid (693-23-2) + aniline (62-53-3) → N1,N12-diphenyldodecane-1,12-diamine (190966-17-7)

Conditions	Yield
With tris(2,4-pentanedionato)ruthenium(III); methanesulfonic acid; hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In 1,4-dioxane at 220℃; under 7500.75 Torr; for 42h; Solvent; Autoclave; Inert atmosphere;	95%

1,12-dodecanedioic acid (693-23-2) + 11-amino-N-(strychnin-2-yl)undecanoic acid amide → N1,N12-Bis[N-(strychnine-2-yl)undecanoic Acid Amide-11-yl]dodecanediamide

Conditions	Yield
Stage #1: 1,12-dodecanedioic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: 11-amino-N-(strychnin-2-yl)undecanoic acid amide In dichloromethane at 20℃; for 14h; Inert atmosphere; Cooling with ice;	93%

tri-n-butylbenzylammonium hydroxide (27574-41-0) + 1,12-dodecanedioic acid (693-23-2) → benzyl(tributyl)azanium dodecanedioic acetate

Conditions	Yield
at 20℃; for 12h;	90.55%

1,12-dodecanedioic acid (693-23-2) + diphenylamine (122-39-4) → 11-(acridin-9-yl)undecan-1-oic acid + 1,10-bis(acridin-9-yl)decane

Conditions	Yield
With zinc(II) chloride at 230℃; for 20h; Condensation;	A 90% B 3%
With zinc(II) chloride at 230℃; for 40h; Condensation;	A 12% B 61%

2-methylglutaronitrile (4553-62-2) + 1,12-dodecanedioic acid (693-23-2) → 3-methyl-piperidine-2,6-dione (29553-51-3) + 1,12-dodecanedinitrile (4543-66-2)

Conditions	Yield
With aluminum (III) chloride at 200℃; for 5h;	A 88% B 81%

1-Tetradecanol (112-72-1) + 1,12-dodecanedioic acid (693-23-2) → dimyristyl dodecanedioate (42234-02-6)

Conditions	Yield
With 1-hexadecyl-3-sulfo-1H-imidazol-3-ium chloride In neat (no solvent) at 110℃; for 16h; Green chemistry;	88%

1,12-dodecanedioic acid (693-23-2) + (S)-2-Amino-6-benzyloxycarbonylamino-hexanoic acid ethyl ester; compound with toluene-4-sulfonic acid → Dodecanedioyl-Lys(Z)-OEt

Conditions	Yield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In tetrahydrofuran; chloroform; N,N-dimethyl-formamide 1.) 0 deg C, 4 h, 2. ) room temp., 2 days;	87%

4-[4’’-fluoro-3’’-(piperazine-1’’’-carbonyl)benzyl]-2H-phthalazin-1-one (763111-47-3) + 1,12-dodecanedioic acid (693-23-2) → 12-(4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoyl)piperazin-1-yl)-12-oxododecanoic acid

Conditions	Yield
Stage #1: 1,12-dodecanedioic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: 4-[4’’-fluoro-3’’-(piperazine-1’’’-carbonyl)benzyl]-2H-phthalazin-1-one In N,N-dimethyl-formamide at 20℃; for 16h;	87%

1,12-dodecanedioic acid (693-23-2) + 3β-hydroxy-14β,16β-O-(4-methoxybenzylidene)card-20(22)-enolide (190579-30-7) → hydrogen 14β,16β-O-(4-methoxybenzylidene)card-20(22)-enolide-3β-yl 1,10-decanedicarboxylate (190579-38-5)

Conditions	Yield
With pyridine; p-toluenesulfonyl chloride for 4h; Ambient temperature;	86%

1,12-dodecanedioic acid (693-23-2) → diperoxydodecanedioic acid (66280-55-5)

Conditions	Yield
With sulfuric acid; dihydrogen peroxide at 15 - 20℃; for 5h;	85%
With dihydrogen peroxide In sulfuric acid at 20℃; for 4h;	49%
With sulfuric acid; dihydrogen peroxide

Upstream product

• 24772-63-2 1,8-diiodooctane 
• 996-82-7 sodium diethylmalonate 
• 830-13-7 cyclododecanone 
• 111-81-9 Methyl 10-undecenoate 
• 67-64-1 acetone 
• 19025-38-8 2-hydroxycyclododecanone 
• 26307-31-3 2-Acetoxycyclododecanone 
• 64-19-7 acetic acid 
• 505-95-3 12-hydroxydodecanoic acid 
• 956-82-1 3-methylcyclopentadecanone 
• 17385-36-3 [1,1'-bi(cyclohexane)]-2,2'-diol 
• 1724-39-6 cyclododecanol 
• 62791-22-4 tert-butyl(cyclohex-1-en-1-yloxy)dimethylsilane 
• 1501-82-2 cyclododecene 

Downstream Products

• 124-04-9 Adipic acid 
• 66280-55-5 diperoxydodecanedioic acid 
• 646-25-3 diaminodecane 
• 4543-66-2 1,12-dodecanedinitrile 
• 4834-98-4 1,12-dodecanedioyl dichloride 
• 1731-79-9 dodecanedioic acid dimethyl ester 
• 15677-90-4 dibutyl dodecanedioate 
• 132505-72-7 Dodecanedioic acid monobutyl ester 
• 66003-63-2 1,12-dodecadicarboxylic acid monoethyl ester 
• 88353-04-2 1,12-dodecanedioic acid monobenzyl ester 
• 79275-69-7 Dodecanedioic acid dibenzyl ester 
• 3903-40-0 12-methoxy-12-oxododecanoic acid 
• 234081-98-2 1,10-decanedicarboxylic acid mono-tert-butyl ester 
• 54982-83-1 1,4-dioxacyclohexadecane-5,16-dione 

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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.

Fatty Acid Chain Shortening by a Fungal Peroxygenase

A recently discovered peroxygenase from the fungus Marasmius rotula (MroUPO) is able to catalyze the progressive one-carbon shortening of medium and long-chain mono- and dicarboxylic acids by itself alone, in the presence of H2O2. The mechanism, analyzed using H218O2, starts with an α-oxidation catalyzed by MroUPO generating an α-hydroxy acid, which is further oxidized by the enzyme to a reactive α-keto intermediate whose decarboxylation yields the one-carbon shorter fatty acid. Compared with the previously characterized peroxygenase of Agrocybe aegerita, a wider heme access channel, enabling fatty acid positioning with the carboxylic end near the heme cofactor (as seen in one of the crystal structures available) could be at the origin of the unique ability of MroUPO shortening carboxylic acid chains.