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Homogentisic acid - crystalline, high purity , CAS No.451-13-8

1 Citations
  • crystalline
Item Number
H477453
Grouped product items
SKUSizeAvailabilityPrice Qty
H477453-100mg
100mg
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$318.90
H477453-500mg
500mg
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$1,214.90
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Basic Description

SynonymsHomogentisic acid | 451-13-8 | 2,5-Dihydroxyphenylacetic acid | Alcapton | Homogentisate acid | Homogentisinic acid | 2-(2,5-dihydroxyphenyl)acetic acid | homogentisate | (2,5-Dihydroxyphenyl)acetic acid | Benzeneacetic acid, 2,5-dihydroxy- | 2,5-Dihydroxybenzeneacetic acid |
Specifications & Puritycrystalline
Storage TempStore at 2-8°C
Shipped InWet ice
Product Description

Homogentisic acid (HGA) is an intermediate formed during the catabolism of phenylalanine and tyrosine. Alkaptonuria, a metabolic disorder, is characterized by high levels of HGA in serum and urine due to the deficiency of the enzyme homogentisic acid oxidase, which is involved in the degradation of HGA.

Names and Identifiers

IUPAC Name 2-(2,5-dihydroxyphenyl)acetic acid
INCHI InChI=1S/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
InChi Key IGMNYECMUMZDDF-UHFFFAOYSA-N
Canonical SMILES C1=CC(=C(C=C1O)CC(=O)O)O
Isomeric SMILES C1=CC(=C(C=C1O)CC(=O)O)O
PubChem CID 780
Molecular Weight 168.15
Beilstein 10407
Reaxy-Rn 2692860

Certificates

Certificate of Analysis(COA)

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Chemical and Physical Properties

Melt Point(°C)147 °C

Safety and Hazards(GHS)

Pictogram(s) GHS07
Signal Warning
Hazard Statements

H315:Causes skin irritation

H319:Causes serious eye irritation

H335:May cause respiratory irritation

Precautionary Statements

P261:Avoid breathing dust/fume/gas/mist/vapors/spray.

P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do - continue rinsing.

P280:Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352:IF ON SKIN: wash with plenty of water.

P321:Specific treatment (see ... on this label).

P405:Store locked up.

P501:Dispose of contents/container to ...

P264:Wash hands [and …] thoroughly after handling.

P271:Use only outdoors or in a well-ventilated area.

P304+P340:IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P403+P233:Store in a well-ventilated place. Keep container tightly closed.

P362+P364:Take off contaminated clothing and wash it before reuse.

P264+P265:Wash hands [and …] thoroughly after handling. Do not touch eyes.

P337+P317:If eye irritation persists: Get medical help.

P332+P317:If skin irritation occurs: Get medical help.

P319:Get medical help if you feel unwell.

Reaxy-Rn 2692860
Merck Index 4737

Related Documents

 SDS

 Specification Sheet

Citations of This Product

1. Xianyu Liang,Fan Liu,Yiqun Wan,Xiaoying Yin,Weiting Liu.  (2018-12-16)  Facile synthesis of molecularly imprinted polymers for selective extraction of tyrosine metabolites in human urine..  Journal of chromatography. A,  1587  (34-41).  [PMID:30551942]

References

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2. J D Shoemaker,W H Elliott.  (1991-01-02)  Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease..  Journal of chromatography,  562  ((1-2)): (125-138).  [PMID:2026685]
3. Z L Hegedus,U Nayak.  (1994-05-01)  Homogentisic acid and structurally related compounds as intermediates in plasma soluble melanin formation and in tissue toxicities..  Archives internationales de physiologie, de biochimie et de biophysique,  102  ((3)): (175-181).  [PMID:8000039]
4. S Janocha,W Wolz,S Srsen,K Srsnova,X Montagutelli,J L Guénet,T Grimm,W Kress,C R Müller.  (1994-01-01)  The human gene for alkaptonuria (AKU) maps to chromosome 3q..  Genomics,  19  ((1)): (5-8).  [PMID:8188241]
5. J C Deutsch,C R Santhosh-Kumar.  (1996-02-23)  Quantitation of homogentisic acid in normal human plasma..  Journal of chromatography. B, Biomedical applications,  677  ((1)): (147-151).  [PMID:8925087]
6. Daniela Braconi,Marcella Laschi,Adam M Taylor,Giulia Bernardini,Adriano Spreafico,Laura Tinti,James A Gallagher,Annalisa Santucci.  (2010-07-29)  Proteomic and redox-proteomic evaluation of homogentisic acid and ascorbic acid effects on human articular chondrocytes..  Journal of cellular biochemistry,  111  ((4)): (922-932).  [PMID:20665660]
7. Shahid Ahmed,Zahir Shah,Nadir Ali.  (2010-08-24)  Chronic low backache and stiffness may not be due ankylosing spondylitis..  JPMA. The Journal of the Pakistan Medical Association,  60  ((8)): (681-683).  [PMID:20726204]
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9. Laura Tinti,Adam M Taylor,Annalisa Santucci,Brenda Wlodarski,Peter J Wilson,Jonathan C Jarvis,William D Fraser,John S Davidson,Lakshminarayan R Ranganath,James A Gallagher.  (2010-10-19)  Development of an in vitro model to investigate joint ochronosis in alkaptonuria..  Rheumatology (Oxford, England),  50  ((2)): (271-277).  [PMID:20952450]
10. Valentina Méndez,Loreine Agulló,Myriam González,Michael Seeger.  (2011-03-23)  The homogentisate and homoprotocatechuate central pathways are involved in 3- and 4-hydroxyphenylacetate degradation by Burkholderia xenovorans LB400..  PloS one,  6  ((3)): (e17583-e17583).  [PMID:21423751]
11. Corinne Raspail,Matthieu Graindorge,Yohann Moreau,Serge Crouzy,Bertrand Lefèbvre,Adeline Y Robin,Renaud Dumas,Michel Matringe.  (2011-05-27)  4-hydroxyphenylpyruvate dioxygenase catalysis: identification of catalytic residues and production of a hydroxylated intermediate shared with a structurally unrelated enzyme..  The Journal of biological chemistry,  286  ((29)): (26061-26070).  [PMID:21613226]
12. Trevor F Cox,Lakshminarayan Ranganath.  (2011-07-12)  A quantitative assessment of alkaptonuria: testing the reliability of two disease severity scoring systems..  Journal of inherited metabolic disease,  34  ((6)): (1153-1162).  [PMID:21744089]
13. Lakshminarayan R Ranganath,Trevor F Cox.  (2011-07-13)  Natural history of alkaptonuria revisited: analyses based on scoring systems..  Journal of inherited metabolic disease,  34  ((6)): (1141-1151).  [PMID:21748407]
14. L Tinti,A Spreafico,F Chellini,M Galeazzi,A Santucci.  (2011-08-05)  A novel ex vivo organotypic culture model of alkaptonuria-ochronosis..  Clinical and experimental rheumatology,  29  ((4)): (693-696).  [PMID:21813063]
15. Shahir S Hamdulay,Judith Finegold,Lucinda Boyer,Monica Khanna,Mo Akmal,Amanda Walker,Anne Kinderlerer.  (2011-09-29)  Clinical images: Magnetic resonance imaging appearance of alkaptonuria..  Arthritis and rheumatism,  64  ((1)): (129-129).  [PMID:21953018]
16. Lia Millucci,Adriano Spreafico,Laura Tinti,Daniela Braconi,Lorenzo Ghezzi,Eugenio Paccagnini,Giulia Bernardini,Loredana Amato,Marcella Laschi,Enrico Selvi,Mauro Galeazzi,Alessandro Mannoni,Maurizio Benucci,Pietro Lupetti,Federico Chellini,Maurizio Orlandini,Annalisa Santucci.  (2012-08-02)  Alkaptonuria is a novel human secondary amyloidogenic disease..  Biochimica et biophysica acta,  1822  ((11)): (1682-1691).  [PMID:22850426]
17. Ya-Jun Guo,Gui-Fang Deng,Xiang-Rong Xu,Shan Wu,Sha Li,En-Qin Xia,Fang Li,Feng Chen,Wen-Hua Ling,Hua-Bin Li.  (2012-08-08)  Antioxidant capacities, phenolic compounds and polysaccharide contents of 49 edible macro-fungi..  Food & function,  3  ((11)): (1195-1205).  [PMID:22868715]
18. Marzieh Eslami,Mansoor Namazian,Hamid R Zare.  (2013-02-07)  Electrooxidation of homogentisic acid in aqueous and mixed solvent solutions: experimental and theoretical studies..  The journal of physical chemistry. B,  117  ((9)): (2757-2763).  [PMID:23384055]
19. Wojciech Ostrowski,Anna Wojakowska,Magdalena Grajzer,Maciej Stobiecki.  (2014-07-27)  Mass spectrometric behavior of phenolic acids standards and their analysis in the plant samples with LC/ESI/MS system..  Journal of chromatography. B, Analytical technologies in the biomedical and life sciences,  967  (21-27).  [PMID:25063924]
20. Irena Brčić Karačonji,Karlo Jurica.  (2017-06-01)  Development and Validation of a GC-MS Method for the Analysis of Homogentisic Acid in Strawberry Tree (.  Journal of AOAC International,  100  ((4)): (889-892).  [PMID:28560954]
21. Xianyu Liang,Fan Liu,Yiqun Wan,Xiaoying Yin,Weiting Liu.  (2018-12-16)  Facile synthesis of molecularly imprinted polymers for selective extraction of tyrosine metabolites in human urine..  Journal of chromatography. A,  1587  (34-41).  [PMID:30551942]
22. Xavier Cetó,Núria Serrano,Miriam Aragó,Alejandro Gámez,Miquel Esteban,José Manuel Díaz-Cruz,Oscar Núñez.  (2018-12-21)  Determination of HPLC-UV Fingerprints of Spanish Paprika (Capsicum annuum L.) for Its Classification by Linear Discriminant Analysis..  Sensors (Basel, Switzerland),  18  ((12)):   [PMID:30567367]
23. H P Vasantha Rupasinghe,Indu Parmar,Sandhya V Neir.  (2019-07-19)  Biotransformation of Cranberry Proanthocyanidins to Probiotic Metabolites by Lactobacillus rhamnosus Enhances Their Anticancer Activity in HepG2 Cells In Vitro..  Oxidative medicine and cellular longevity,  2019  (4750795-4750795).  [PMID:31316718]
24. Shuzhang Yang,Sandra M Siepka,Kimberly H Cox,Vivek Kumar,Marleen de Groot,Yogarany Chelliah,Jun Chen,Benjamin Tu,Joseph S Takahashi.  (2019-10-16)  Tissue-specific FAH deficiency alters sleep-wake patterns and results in chronic tyrosinemia in mice..  Proceedings of the National Academy of Sciences of the United States of America,  116  ((44)): (22229-22236).  [PMID:31611405]
25. Damian Tarasek,Beata Gąsowska-Bajger,Hubert Wojtasek.  (2020-03-11)  Mechanisms of interference of p-diphenols with the Trinder reaction..  Bioorganic chemistry,  97  (103692-103692).  [PMID:32155504]
26. Chanika Phornphutkul,Wendy J Introne,Monique B Perry,Isa Bernardini,Mark D Murphey,Diana L Fitzpatrick,Paul D Anderson,Marjan Huizing,Yair Anikster,Lynn H Gerber,William A Gahl.  (2002-12-27)  Natural history of alkaptonuria..  The New England journal of medicine,  347  ((26)): (2111-2121).  [PMID:12501223]
27. E Selvi,E Garcia-Gonzalez,R Maggio,S Lorenzini,A Santucci,M Galeazzi.  (2010-07-28)  False proteinuria in patients with alkaptonuria..  Clinical and experimental rheumatology,  28  ((4)): (591-591).  [PMID:20659416]
28. Efstathios Rallis,Stephanos Kintzoglou.  (2010-08-10)  Ashy ears..  TheScientificWorldJournal,  10  (1530-1531).  [PMID:20694448]
29. Molly Yancovitz,Robert Anolik,Miriam Keltz Pomeranz.  (2010-12-18)  Alkaptonuria..  Dermatology online journal,  16  ((11)): (6-6).  [PMID:21163157]
30. Giovanni Concistrè,Brenno Fiorani,Federico Ranocchi,Giovanni Casali,Antonio Loforte,Francesco Musumeci.  (2011-03-19)  Black aorta in a patient with alkaptonuria (ochronosis)..  Journal of cardiovascular medicine (Hagerstown, Md.),  12  ((6)): (444-445).  [PMID:21415764]
31. Andrea Zatkova.  (2011-07-02)  An update on molecular genetics of Alkaptonuria (AKU)..  Journal of inherited metabolic disease,  34  ((6)): (1127-1136).  [PMID:21720873]
32. Daniela Braconi,Claretta Bianchini,Giulia Bernardini,Marcella Laschi,Lia Millucci,Adriano Spreafico,Annalisa Santucci.  (2011-08-30)  Redox-proteomics of the effects of homogentisic acid in an in vitro human serum model of alkaptonuric ochronosis..  Journal of inherited metabolic disease,  34  ((6)): (1163-1176).  [PMID:21874298]
33. A M Taylor,A Boyde,P J M Wilson,J C Jarvis,J S Davidson,J A Hunt,L R Ranganath,J A Gallagher.  (2011-12-01)  The role of calcified cartilage and subchondral bone in the initiation and progression of ochronotic arthropathy in alkaptonuria..  Arthritis and rheumatism,  63  ((12)): (3887-3896).  [PMID:22127706]
34. Huaixin Zheng,Christa H Chatfield,Mark R Liles,Nicholas P Cianciotto.  (2013-08-28)  Secreted pyomelanin of Legionella pneumophila promotes bacterial iron uptake and growth under iron-limiting conditions..  Infection and immunity,  81  ((11)): (4182-4191).  [PMID:23980114]
35. Muhammad Saqib,Shahid Iqbal,Sumaira Naeem,Asif Mahmood.  (2013-11-06)  DFT for exploring the antioxidant potential of homogentisic and orsellinic acids..  Pakistan journal of pharmaceutical sciences,  26  ((6)): (1209-1214).  [PMID:24191328]
36. Dominik Szwajgier.  (2015-12-29)  Anticholinesterase activity of selected phenolic acids and flavonoids - interaction testing in model solutions..  Annals of agricultural and environmental medicine : AAEM,  22  ((4)): (690-694).  [PMID:26706979]
37. Yaping Wang,Chao Yang,Wen Xue,Ting Zhang,Xipei Liu,Jiansong Ju,Baohua Zhao,Dong Liu.  (2017-05-27)  Selection and characterization of alanine racemase inhibitors against Aeromonas hydrophila..  BMC microbiology,  17  ((1)): (122-122).  [PMID:28545531]
38. Maria Lucia Schiavone,Alessandra Pecorelli,Brittany Woodby,Francesca Ferrara,Erika Pambianchi,Annalisa Santucci,Giuseppe Valacchi.  (2020-06-06)  Mechanisms involved in the unbalanced redox homeostasis in osteoblastic cellular model of Alkaptonuria..  Archives of biochemistry and biophysics,  690  (108416-108416).  [PMID:32502471]

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