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Cas Database

77-92-9

77-92-9

Identification

  • Product Name:Citric acid

  • CAS Number: 77-92-9

  • EINECS:201-069-1

  • Molecular Weight:193.117

  • Molecular Formula: C6H8O7

  • HS Code:2918.14 Oral rat LD50: 3000 mg/kg

  • Mol File:77-92-9.mol

Synonyms:Citretten;.beta.-Hydroxytricarballylic acid;K-Lyte;Citric Acid anhy;2-Hydroxy-1,2, 3-propanetricarboxylic acid;K-Lyte/Cl;Kyselina 2-hydroxy-1,2,3-propantrikarbonova [Czech];2-Hydroxypropanetricarboxylic acid;Chemfill;Citric acid (8CI);2-Hydroxy-1,2,3-propanetricarboxylic acid;3-Carboxy-3-hydroxypentane-1,5-dioic acid;Anhydrous citric acid;1,2,3-Propanetricarboxylic acid,2-hydroxy-;2-hydroxypropane-1,2,3-tricarboxylate;Anhydrous citric acid (JP14);Kyselina citronova [Czech];H3cit;FEMA No. 2306;E 330;2-Hydroxytricarballylic acid;F 0001 (polycarboxylic acid);Kyselina citronova;Hydrocerol A;Citric acid [USAN:JAN];Citric acid, anhydrous;1,2,3-Propanetricarboxylic acid, 2-hydroxy- (9CI);Uro-trainer;1,2,3-Propanetricarboxylic acid, 2-hydroxy-;Aciletten;Monohydrate Citric Acid;Citric acid anhydrate;Citric Acid Anydrous;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi,CorrosiveC

  • Hazard Codes:Xi,C,T

  • Signal Word:No signal word.

  • Hazard Statement:none

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Refer for medical attention. In case of skin contact Rinse skin with plenty of water or shower. Refer for medical attention . In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Refer for medical attention . Inhalation of dust irritates nose and throat. Contact with eyes causes irritation. (USCG, 1999) /SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Organic acids and related compounds/

  • Fire-fighting measures: Suitable extinguishing media Extinguish with/ water, foam, dry chem, carbon dioxide. Behavior in Fire: Melts and decomposes. The reaction is not hazardous. (USCG, 1999) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Wash away remainder with plenty of water. Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Wash away remainder with plenty of water.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Separated from strong oxidants, strong bases, metal nitrates and metals. Dry.Crystalline citric acid, anhydrous, can be stored in dry form without difficulty, although conditions of high humidity and elevated temperatures should be avoided to prevent caking. Storage should be in tight containers to prevent exposure to moist air. Several granulations are commercially available with the larger particle sizes having less tendency toward caking.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:Usbiological
  • Product Description:Citric Acid, Anhydrous, ACS
  • Packaging:500g
  • Price:$ 73
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:Citric acid
  • Packaging:10g
  • Price:$ 45
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  • Manufacture/Brand:Tocris
  • Product Description:Citric acid ≥99.5%
  • Packaging:500G
  • Price:$ 46
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Citric Acid >98.0%(T)
  • Packaging:500g
  • Price:$ 29
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Citric acid ACS reagent, ≥99.5%
  • Packaging:2.5kg
  • Price:$ 280
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Citric acid anhydrous powder EMPROVE? EXPERT Ph Eur,BP,JP,USP,ACS
  • Packaging:1370025000
  • Price:$ 273
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Citric acid ≥99.5%, FCC, FG
  • Packaging:25 kg
  • Price:$ 271
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Citric acid ≥99.5%, FCC, FG
  • Packaging:25kg-k
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Citric acid ≥99.5%, FCC, FG
  • Packaging:10kg-k
  • Price:$ 250
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Citric acid anhydrous for synthesis. CAS 77-92-9, chemical formula (HOOCCH ) C(OH)COOH., anhydrous for synthesis
  • Packaging:8187075000
  • Price:$ 242
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Relevant articles and documentsAll total 40 Articles be found

-

Warneford,Hardy

, (1926)

-

Biosynthesis of isocitric acid in repeated-batch culture and testing of its stress-protective activity

Morgunov, Igor G.,Kamzolova, Svetlana V.,Karpukhina, Olga V.,Bokieva, Svetlana B.,Inozemtsev, Anatoly N.

, (2019)

Biosynthesis of Ds(+)-threo-isocitric acid from ethanol in the Yarrowia lipolytica batch and repeated-batch cultures was studied. Repeated-batch cultivation was found to provide for a good biosynthetic efficiency of the producer for as long as 748?h, probably due to maintenance of high activities of enzymes involved in the biosynthesis of isocitric acid. Under optimal repeated-batch cultivation conditions, the producer accumulated 109.6?g/L Ds(+)-threo-isocitric acid with a production rate of 1.346?g/L?h. The monopotassium salt of isocitric acid isolated from the culture liquid and purified to 99.9% was found to remove neurointoxication, to restore memory, and to improve the learning of laboratory rats intoxicated with lead and molybdenum salts. Taking into account the fact that the neurotoxic effect of heavy metals is mainly determined by oxidative stress, the aforementioned favorable action of isocitric acid on the intoxicated rats can be explained by its antioxidant activity among other pharmacological effects.

Discovery and Biosynthesis of Bolagladins: Unusual Lipodepsipeptides from Burkholderia gladioli Clinical Isolates**

Challis, Gregory L.,Dashti, Yousef,Jian, Xinyun,Mahenthiralingam, Eshwar,Mullins, Alex J.,Nakou, Ioanna T.,Webster, Gordon

, (2020)

Two Burkholderia gladioli strains isolated from the lungs of cystic fibrosis patients were found to produce unusual lipodepsipeptides containing a unique citrate-derived fatty acid and a rare dehydro-β-alanine residue. The gene cluster responsible for the

-

Wehmer

, p. 37 (1913)

-

SYNTHESIS OF 4-(HYDROXYMETHYL)TETRAHYDRO-4-PYRANOL - A NEW INTERMEDIATE FOR THE PREPARATION OF SYNTHETIC CITRIC ACID

Gevorkyan, A. A.,Kazaryan, P. I.,Sargysyan, M. S.,Petrosyan, K. A.,Mkrtumyan, S. A.

, p. 712 - 713 (1983)

The hydroxylation of 4-methylenetetrahydropyran with hydrogen peroxide in the presence of various acidic catalysts was investigated.The oxidation of 4-(hydroxymethyl)tetrahydro-4-pyranol with concentrated nitric acid leads to citric acid in 50percent yield.

Citric acid production from xylan and xylan hydrolysate by semi-solid culture of Aspergillus niger

Kirimura, Kohtaro,Watanabe, Taisei,Sunagawa, Tadahiro,Usami, Shoji

, p. 226 - 228 (1999)

Citric acid production from xylan and xylan hydrolysate was done by Aspergillus niger Yang no. 2 cultivated in a semi-solid culture using bagasse as a carrier. Yang no. 2 produced 72.4 g/l and 52.6 g/l of citric acid in 5 d from 140 g/l of xylose and arabinose, respectively. Yang no. 2 produced 51.6 g/l of citric acid in 3 d from a concentrated xylan hydrolysate prepared by cellulase treatment, containing 100 g/l of reducing sugars. Moreover, Yang no. 2 directly produced 39.6 g/l of citric acid maximally in 3 d from 140 g/l of xylan.

Absolute stereochemical course of the 3-carboxymuconate cycloisomerases from Pseudomonas putida and Acinetobacter colcoaceticus: Analysis and implications

Chari,Whitman,Kozarich,et al.

, p. 5514 - 5519 (1987)

The absolute stereochemical course of the 3-carboxymuconate cycloisomerases [EC 5.5.1.2; 2-carboxy-5-oxo-2,5-dihydrofuran-2-acetate lyase (decyclizing)] from Pseudomonas putida and Acinetobacter calcoaceticus has been determined by chemical and 1H NMR methods. The product of the enzyme-catalyzed reaction in 2H2O was detected by NMR and trapped by catalytic hydrogenation to afford 5-[2H]homocitrate lactone. Subsequent chemical degradation of the monodeuteriated homocitrate lactone gave (2r,3S)-2-[2H]citrate as determined by 1H NMR analysis. The product of the cycloisomerase reaction was established as (4R,5R)-5-[2H]-4-carboxymuconate, indicating that the lactonization proceeded by an anti addition - the mechanistic and stereochemical antipode of the previously studied muconate cycloisomerase from P. putida and 3-carboxymuconate cycloisomerase from Neurospora crassa. The anti addition probably represents the lower energy pathway for the reaction and suggests that the evolutionary relationship between the two classes of cycloisomerases is more remote than previously believed.

ACIDIC Nα-ACYLARGININE DERIVATIVES IN ARGININE-ACCUMUTATING PLANT TISSUES

Kasai, Takanori,Shiroshita, Yoshinari,Uomoto, Katsuhito,Sakamura, Sadao

, p. 147 - 150 (1983)

Two new acidic Nα-acylarginine derivatives were isolated from arginin-accumulating plant tissues.The first, Nα-(2-hydroxy-2-carboxymethylsuccinyl)-L-arginine, was isolated from bulbs of Lilium maximowiczii, whilst the second, Nα-(2-hydroxysuccinyl)arginine, was obtained from tubers of Smilax china and seeds of Vicia faba.No acidic Nα-acylarginine derivatives was detected, however, in roots of Rumex obtusifolius which contained fairly large amounts of arginine and malonic acid.Key Wors Index: Lilium maximowiczii; Smilax china; Vicia faba; Rumex obtusifolius;Liliaceae; Leguminosae; Polygonacea; acylarginine derivatives; Nα-(2-hydroxy-2-carboxymethylsuccinyl)-L-arginine; Nα-(2-hydroxysuccinyl)arginine

Kusnetzow

, p. 341 (1925)

-

Salmony

, p. 902 (1927)

-

Stern et al.

, (1956)

Citrate inhibition of cisplatin reaction with DNA studied using fluorescently labeled oligonucleotides: Implication for selectivity towards guanine

Wang, Feng,Huang, Po-Jung Jimmy,Liu, Juewen

, p. 9482 - 9484 (2013)

The reaction between cisplatin and DNA is conveniently studied using fluorescently labeled oligonucleotides and gel electrophoresis; as an example of application, the inhibition of this reaction by citrate is demonstrated, which might increase selectivity

Cyanide as a primordial reductant enables a protometabolic reductive glyoxylate pathway

Krishnamurthy, Ramanarayanan,Pulletikurti, Sunil,Yadav, Mahipal,Yerabolu, Jayasudhan R.

, p. 170 - 178 (2022/02/11)

Investigation of prebiotic metabolic pathways is predominantly based on abiotically replicating the reductive citric acid cycle. While attractive from a parsimony point of view, attempts using metal/mineral-mediated reductions have produced complex mixtures with inefficient and uncontrolled reactions. Here we show that cyanide acts as a mild and efficient reducing agent mediating abiotic transformations of tricarboxylic acid intermediates and derivatives. The hydrolysis of the cyanide adducts followed by their decarboxylation enables the reduction of oxaloacetate to malate and of fumarate to succinate, whereas pyruvate and α-ketoglutarate themselves are not reduced. In the presence of glyoxylate, malonate and malononitrile, alternative pathways emerge that bypass the challenging reductive carboxylation steps to produce metabolic intermediates and compounds found in meteorites. These results suggest a simpler prebiotic forerunner of today’s metabolism, involving a reductive glyoxylate pathway without oxaloacetate and α-ketoglutarate—implying that the extant metabolic reductive carboxylation chemistries are an evolutionary invention mediated by complex metalloproteins. [Figure not available: see fulltext.].

Bacterial flavoprotein monooxygenase YxeK salvages toxic S-(2-succino)-adducts via oxygenolytic C–S bond cleavage

Ellis, Holly R.,Kammerer, Bernd,Lagies, Simon,Matthews, Arne,Sch?nfelder, Julia,Schleicher, Erik,Stull, Frederick,Teufel, Robin

, (2021/10/06)

Thiol-containing nucleophiles such as cysteine react spontaneously with the citric acid cycle intermediate fumarate to form S-(2-succino)-adducts. In Bacillus subtilis, a salvaging pathway encoded by the yxe operon has recently been identified for the detoxification and exploitation of these compounds as sulfur sources. This route involves acetylation of S-(2-succino)cysteine to N-acetyl-2-succinocysteine, which is presumably converted to oxaloacetate and N-acetylcysteine, before a final deacetylation step affords cysteine. The critical oxidative cleavage of the C–S bond of N-acetyl-S-(2-succino)cysteine was proposed to depend on the predicted flavoprotein monooxygenase YxeK. Here, we characterize YxeK and verify its role in S-(2-succino)-adduct detoxification and sulfur metabolism. Detailed biochemical and mechanistic investigation of YxeK including 18O-isotope-labeling experiments, homology modeling, substrate specificity tests, site-directed mutagenesis, and (pre-)steady-state kinetics provides insight into the enzyme’s mechanism of action, which may involve a noncanonical flavin-N5-peroxide species for C–S bond oxygenolysis.

Catalytic Oxidation of VOCs over SmMnO3 Perovskites: Catalyst Synthesis, Change Mechanism of Active Species, and Degradation Path of Toluene

Liu, Lizhong,Sun, Jiangtian,Ding, Jiandong,Zhang, Yan,Jia, Jinping,Sun, Tonghua

, p. 14275 - 14283 (2019/10/17)

Highly active samarium manganese perovskite oxides were successfully prepared by employing self-molten-polymerization, coprecipitation, sol-gel, and impregnation methods. The physicochemical properties of perovskite oxides were investigated by XRD, N2 adsorption-desorption, XPS, and H2-TPR. Their catalytic performances were compared via the catalytic oxidation of toluene. The perovskite prepared by self-molten-polymerization possessed the highest catalytic capacity, which can be ascribed to its higher oxygen adspecies concentration (Olatt/Oads = 0.53), higher surface Mn4+/Mn3+ ratio (Mn4+/Mn3+ = 0.95), and best low-temperature reducibility (H2 consumption = 0.27; below 350 °C). The most active catalyst also exhibited good cycling and long-term stability for toluene oxidation. After a multistep cycle reaction and a long-term reaction of 42 h, the toluene conversion maintained above 99.9% at 270 °C. Mechanistic study hinted that lattice oxygen was involved in toluene oxidation. The oxidation reaction was dependent on the synergism of lattice oxygen, adsorbed oxygen, and oxygen vacancies. The degradation pathway of toluene, researched by diffuse reflectance infrared Fourier transform spectroscopy and online mass spectrometry technologies, demonstrated that a series of organic byproducts existed at a relatively low temperature. This work provides an efficient and practical method for selecting highly active catalysts and for exploring the catalytic mechanism for the removal of atmospheric environmental pollution.

Highly Active Mn3-xFexO4 Spinel with Defects for Toluene Mineralization: Insights into Regulation of the Oxygen Vacancy and Active Metals

Liu, Lizhong,Sun, Jiangtian,Ding, Jiandong,Zhang, Yan,Sun, Tonghua,Jia, Jinping

supporting information, p. 13241 - 13249 (2019/10/21)

A series of highly defected Mn3-xFexO4 spinels with different amounts of oxygen vacancies and active metals were successfully synthesized by regulating the insertion of Fe ions into the crystal structure of Mn3O4 via self-polymerizable monomer adjustment of the molten Mn-Fe salt dispersion. The characterization of X-ray diffraction, Raman, scanning electron microscopy, X-ray photoelectron spectroscopy, and N2 adsorption-desorption showed that the doping of Fe increased the lattice defects, oxygen vacancy concentration, specific surface area, mesoporosity, and catalytic properties compared to Cu ions doping. Temperature-programmed reduction with hydrogen and oxygen pulse chemisorption tests determined that the doping level of Fe ions had an important influence on the oxygen vacancy content and the dispersion of active metals on the catalysts' surfaces. For the best Mn-dispersed and most active Mn2.4Fe0.6O4 catalyst, a long-term toluene oxidation measurement running for 120 h of uninterrupted reaction, at the low temperature of 240 °C, high humidity (relative humidity = 100%), and high weight hourly space velocity of 60000 mL·g-1·h-1, was also carried out, which indicated that the catalyst possessed high stability and endurability. Moreover, the continuous oxidation route and internal principle for toluene oxidation were also revealed by the in situ diffuse-reflectance infrared Fourier transform spectroscopy and gas chromatography-mass spectrometry techniques and deep dynamics study.

Process route upstream and downstream products

Process route

carbon dioxide
124-38-9,18923-20-1

carbon dioxide

2-buten-4-olide
497-23-4

2-buten-4-olide

benzaldehyde
100-52-7

benzaldehyde

acetic acid
64-19-7,77671-22-8

acetic acid

benzoic acid
65-85-0,8013-63-6

benzoic acid

Conditions
Conditions Yield
With SmMnO3; at 350 ℃; Temperature; Reagent/catalyst; Catalytic behavior;
With Fe0.6Mn2.4O4; for 120h; Reagent/catalyst; Catalytic behavior;
β-D-glucose
492-61-5

β-D-glucose

1-hydroxy-propane-1,2,3-tricarboxylic acid
320-77-4

1-hydroxy-propane-1,2,3-tricarboxylic acid

2-methylisocitric acid

2-methylisocitric acid

Conditions
Conditions Yield
With Saccharomycopsis lipolytica; In water; at 26 ℃; for 120h; Product distribution; also in n-hexadecane medium; catabolism of amino acids by S. lipolytica;
β-D-glucose
492-61-5

β-D-glucose

1-hydroxy-propane-1,2,3-tricarboxylic acid
320-77-4

1-hydroxy-propane-1,2,3-tricarboxylic acid

2-methylisocitric acid

2-methylisocitric acid

Conditions
Conditions Yield
With Saccharomycopsis lipolytica; In water; at 26 ℃; for 120h; Product distribution; also in n-hexadecane medium; catabolism of amino acids by S. lipolytica;
β-D-glucose
492-61-5

β-D-glucose

1-hydroxy-propane-1,2,3-tricarboxylic acid
320-77-4

1-hydroxy-propane-1,2,3-tricarboxylic acid

2-methylisocitric acid

2-methylisocitric acid

Conditions
Conditions Yield
With Saccharomycopsis lipolytica; In water; at 26 ℃; for 120h; Product distribution; also in n-hexadecane medium; catabolism of amino acids by S. lipolytica;
β-D-glucose
492-61-5

β-D-glucose

1-hydroxy-propane-1,2,3-tricarboxylic acid
320-77-4

1-hydroxy-propane-1,2,3-tricarboxylic acid

2-methylisocitric acid

2-methylisocitric acid

Conditions
Conditions Yield
With Saccharomycopsis lipolytica; In water; at 26 ℃; for 120h; Product distribution; also in n-hexadecane medium; catabolism of amino acids by S. lipolytica;
β-D-glucose
492-61-5

β-D-glucose

1-hydroxy-propane-1,2,3-tricarboxylic acid
320-77-4

1-hydroxy-propane-1,2,3-tricarboxylic acid

2-methylisocitric acid

2-methylisocitric acid

Conditions
Conditions Yield
With Saccharomycopsis lipolytica; In water; at 26 ℃; for 120h; Product distribution; also in n-hexadecane medium; catabolism of amino acids by S. lipolytica;
β-D-glucose
492-61-5

β-D-glucose

1-hydroxy-propane-1,2,3-tricarboxylic acid
320-77-4

1-hydroxy-propane-1,2,3-tricarboxylic acid

2-methylisocitric acid

2-methylisocitric acid

Conditions
Conditions Yield
With Saccharomycopsis lipolytica; In water; at 26 ℃; for 120h; Product distribution; also in n-hexadecane medium; catabolism of amino acids by S. lipolytica;
Hexadecane
544-76-3

Hexadecane

1-hydroxy-propane-1,2,3-tricarboxylic acid
320-77-4

1-hydroxy-propane-1,2,3-tricarboxylic acid

2-methylisocitric acid

2-methylisocitric acid

Conditions
Conditions Yield
With Saccharomycopsis lipolytica; In water; at 26 ℃; for 192h; Product distribution; catabolism of amino acids by S. lipolytica;
Hexadecane
544-76-3

Hexadecane

1-hydroxy-propane-1,2,3-tricarboxylic acid
320-77-4

1-hydroxy-propane-1,2,3-tricarboxylic acid

2-methylisocitric acid

2-methylisocitric acid

Conditions
Conditions Yield
With Saccharomycopsis lipolytica; In water; at 26 ℃; for 192h; Product distribution; catabolism of amino acids by S. lipolytica;
Hexadecane
544-76-3

Hexadecane

1-hydroxy-propane-1,2,3-tricarboxylic acid
320-77-4

1-hydroxy-propane-1,2,3-tricarboxylic acid

2-methylisocitric acid

2-methylisocitric acid

Conditions
Conditions Yield
With Saccharomycopsis lipolytica; In water; at 26 ℃; for 192h; Product distribution; catabolism of amino acids by S. lipolytica;

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