4-hydroxymandelic acid (BioDeep_00000001255)

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite PANOMIX_OTCML-2025


代谢物信息卡片


(2S)-hydroxy(4-hydroxyphenyl)ethanoic acid

  化学式: C8H8O4 (168.0423)
中文名称: 4-羟基扁桃酸, 对羟基扁桃酸, 4-羟基苯基乙醇酸
  谱图信息: 最多检出来源 Homo sapiens(feces) 16.35%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

4-hydroxymandelic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/4-hydroxymandelic_acid (retrieved 2025-07-27) (BioDeep RN: BioDeep_00000001255). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1=CC(=CC=C1C(C(=O)O)O)O
InChI: InChI=1S/C8H8O4/c9-6-3-1-5(2-4-6)7(10)8(11)12/h1-4,7,9-10H,(H,11,12)/t7-/m0/s1

描述信息

p-Hydroxymandelic acid, also known as 4-hydroxymandelate or 4-hydroxyphenylglycolate, belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. p-Hydroxymandelic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make p-hydroxymandelic acid a potential biomarker for the consumption of these foods. p-Hydroxymandelic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on p-Hydroxymandelic acid.
p-Hydroxymandelic acid is a valuable aromatic fine chemical and widely used for production of pharmaceuticals and food additives.

同义名列表

72 个代谢物同义名

(2S)-hydroxy(4-hydroxyphenyl)ethanoic acid; 4-Hydroxyphenylglycolic acid; p-Hydroxymandelic acid; L-4-Hydroxymandelate; L-p-Hydroxymandelate; p-Hydroxymandelic acid; 4-Hydroxymandelate; 2-Hydroxy-2-(4'-hydroxyphenyl)acetic acid; 4-Hydroxyphenylglycolic acid; .alpha.,4-Dihydroxybenzeneacetic acid; (+-)-4-Hydroxymandelic acid; (+-)-alpha,4-Dihydroxybenzeneacetic acid; (+-)-p-Hydroxymandelic acid; (+/-)-.ALPHA.,4-DIHYDROXYBENZENEACETIC ACID; (+/-)-4-hydroxymandelic acid; (+/-)-alpha,4-dihydroxy-Benzeneacetate; (+/-)-alpha,4-dihydroxy-Benzeneacetic acid; (+/-)-P-HYDROXYMANDELIC ACID; (RS)-p-Hydroxymandelate; (RS)-p-Hydroxymandelic acid; 2-(4-Hydroxyphenyl)-2-hydroxyacetate; 2-(4-Hydroxyphenyl)-2-hydroxyacetic acid; 2-(4-hydroxyphenyl)-2-oxidanyl-ethanoic acid; 2-(4'-hydroxyphenyl)-2-hydroxyethanoic acid; 2-hydroxy-2-(4-hydroxyphenyl)acetic acid; 2-hydroxy-2-(4-hydroxyphenyl)aceticacid; 4-HMA; 4-Hydroxy-DL-mandelate; 4-Hydroxy-DL-mandelic acid; 4-hydroxy-mandelic acid; 4-hydroxymandelic acid; 4-hydroxymandelic acid, (D)-isomer; 4-Hydroxyphenylglycolate; 4'-Hydroxymandelic acid; alpha,4-dihydroxy-Benzeneacetate; alpha,4-dihydroxy-Benzeneacetic acid; alpha,4-Dihydroxybenzeneacetate; alpha,4-Dihydroxybenzeneacetic acid; Benzeneacetic acid, ?,4-dihydroxy-; Benzeneacetic acid, .alpha.,4-dihydroxy-; Benzeneacetic acid, alpha,4-dihydroxy-; delta-4-hydroxymandelate; delta-p-hydroxymandelate; DL-4-Hydroxymandelate; DL-4-Hydroxymandelic acid; Dl-4-hydroxymandelicacid; DL-alpha,4-Dihydroxyphenylacetic Acid; DL-p-Hydroxymandelate; DL-p-Hydroxymandelic acid; DL-p-Hydroxyphenylglycolate; DL-p-Hydroxyphenylglycolic acid; HV52GS53BA; Hydroxy(4-hydroxyphenyl)acetic acid; Mandelic acid, p-hydroxy-; p-hydroxy-Mandelate; p-hydroxy-Mandelic acid; p-Hydroxymandelate; p-Hydroxymandelic acid (PHMA); p-Hydroxyphenylglycolate; p-Hydroxyphenylglycolic acid; para-hydroxymandelic acid; parahydroxymandelic acid; pisolithin B; racemic parahydroxymandelic acid; UNII-HV52GS53BA; (R)-4-Hydroxymandelate; (S)-4-Hydroxymandelate; 3-Dimethylallyl-4-hydroxymandelate; 3-Dimethylallyl-4-hydroxymandelic acid; D-4-Hydroxymandelate; D-p-Hydroxymandelate; Hydroxy(4-hydroxyphenyl)acetate



数据库引用编号

20 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome()

BioCyc()

PlantCyc()

代谢反应

个相关的代谢反应过程信息。

Reactome()

BioCyc()

WikiPathways()

Plant Reactome()

INOH()

PlantCyc()

COVID-19 Disease Map()

PathBank()

PharmGKB()

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:

  • PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 5 AXIN2, DAO, DBH, HPD, TYR
Peripheral membrane protein 3 DAO, HPD, HSD17B6
Endoplasmic reticulum membrane 1 HPD
Nucleus 1 AXIN2
cytosol 3 AXIN2, DAO, HPD
centrosome 1 AXIN2
Cell membrane 2 DAO, PHEX
Early endosome membrane 1 HSD17B6
Golgi apparatus membrane 1 HPD
Synapse 1 DBH
glutamatergic synapse 1 GHRL
Golgi apparatus 1 PHEX
Golgi membrane 2 HPD, INS
lysosomal membrane 1 CP
postsynapse 1 GHRL
Cytoplasm, cytosol 1 DAO
Lysosome 1 TYR
plasma membrane 4 AXIN2, CP, DAO, PHEX
presynaptic active zone 1 DAO
Membrane 2 DBH, PHEX
axon 1 GHRL
extracellular exosome 3 CP, DAO, HPD
Lumenal side 1 HSD17B6
endoplasmic reticulum 3 DBH, HSD17B6, PHEX
extracellular space 6 CP, DAO, DBH, GHRL, INS, PYY
perinuclear region of cytoplasm 2 PHEX, TYR
Schaffer collateral - CA1 synapse 1 GHRL
bicellular tight junction 1 DAO
intracellular membrane-bounded organelle 3 DBH, HSD17B6, TYR
Microsome membrane 1 HSD17B6
Single-pass type I membrane protein 1 TYR
Secreted 5 CP, DAO, DBH, GHRL, INS
extracellular region 6 CP, DAO, DBH, GHRL, INS, PYY
Extracellular side 1 DAO
centriolar satellite 1 DBH
neuronal dense core vesicle lumen 1 GHRL
beta-catenin destruction complex 1 AXIN2
Melanosome membrane 1 TYR
Golgi-associated vesicle 1 TYR
Single-pass type II membrane protein 2 DBH, PHEX
Peroxisome 1 DAO
Peroxisome matrix 1 DAO
peroxisomal matrix 1 DAO
cell projection 1 DAO
Secreted, extracellular space 1 DAO
blood microparticle 1 CP
endosome lumen 1 INS
Melanosome 1 TYR
secretory granule lumen 3 DBH, GHRL, INS
secretory granule membrane 1 DBH
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 CP, GHRL, INS
specific granule lumen 1 DAO
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
Cytoplasmic vesicle, secretory vesicle membrane 1 DBH
Cytoplasmic vesicle, secretory vesicle, chromaffin granule lumen 1 DBH
chromaffin granule lumen 1 DBH
transport vesicle membrane 1 DBH
[Soluble dopamine beta-hydroxylase]: Cytoplasmic vesicle, secretory vesicle lumen 1 DBH
Cytoplasmic vesicle, secretory vesicle, chromaffin granule membrane 1 DBH
chromaffin granule membrane 1 DBH


文献列表

  • Jorge Gutiérrez-Hellín, Juan José Salinero, Javier Abían-Vicen, Francisco Areces, Beatriz Lara, Cesar Gallo, Carlos Puente, Juan Del Coso. Acute consumption of p-synephrine does not enhance performance in sprint athletes. Applied physiology, nutrition, and metabolism = Physiologie appliquee, nutrition et metabolisme. 2016 Jan; 41(1):63-9. doi: 10.1139/apnm-2015-0299. [PMID: 26673246]
  • Zhoutong Sun, Yuanyuan Ning, Lixia Liu, Yingmiao Liu, Bingbing Sun, Weihong Jiang, Chen Yang, Sheng Yang. Metabolic engineering of the L-phenylalanine pathway in Escherichia coli for the production of S- or R-mandelic acid. Microbial cell factories. 2011 Sep; 10(?):71. doi: 10.1186/1475-2859-10-71. [PMID: 21910908]
  • Ferdinand A van Dorsten, Christian H Grün, Ewoud J J van Velzen, Doris M Jacobs, Richard Draijer, John P M van Duynhoven. The metabolic fate of red wine and grape juice polyphenols in humans assessed by metabolomics. Molecular nutrition & food research. 2010 Jul; 54(7):897-908. doi: 10.1002/mnfr.200900212. [PMID: 20013882]
  • Kyung-Bum Lee, Philippe De Backer, Toshihiro Aono, Chi-Te Liu, Shino Suzuki, Tadahiro Suzuki, Takakazu Kaneko, Manabu Yamada, Satoshi Tabata, Doris M Kupfer, Fares Z Najar, Graham B Wiley, Bruce Roe, Tim T Binnewies, David W Ussery, Wim D'Haeze, Jeroen Den Herder, Dirk Gevers, Danny Vereecke, Marcelle Holsters, Hiroshi Oyaizu. The genome of the versatile nitrogen fixer Azorhizobium caulinodans ORS571. BMC genomics. 2008 Jun; 9(?):271. doi: 10.1186/1471-2164-9-271. [PMID: 18522759]
  • Satyanarayana Sreemantula, Srinivas Nammi, Rajabhanu Kolanukonda, Sushruta Koppula, Krishna M Boini. Adaptogenic and nootropic activities of aqueous extract of Vitis vinifera (grape seed): an experimental study in rat model. BMC complementary and alternative medicine. 2005 Jan; 5(?):1. doi: 10.1186/1472-6882-5-1. [PMID: 15656916]
  • K Arai, D Jin, F Kusu, K Takamura. Determination of p-hydroxymandelic acid enantiomers in urine by high-performance liquid chromatography with electrochemical detection. Journal of pharmaceutical and biomedical analysis. 1997 Jun; 15(9-10):1509-14. doi: 10.1016/s0731-7085(97)00038-1. [PMID: 9226583]
  • J M Midgley, R Andrew, D G Watson, N MacDonald, J L Reid, D A Williams. Dichlorotetrafluoroacetone as a derivatisation reagent in the analysis of mandelic acids in human urine. Journal of chromatography. 1990 May; 527(2):259-65. doi: 10.1016/s0378-4347(00)82110-6. [PMID: 2387876]
  • M W Couch, D M Greer, C M Williams. Excretion of octopamine metabolites in neuroblastoma. Clinica chimica acta; international journal of clinical chemistry. 1986 Jul; 158(1):109-14. doi: 10.1016/0009-8981(86)90121-x. [PMID: 3091293]
  • S Higa, S Kishimoto. Isolation of 2-hydroxycarboxylic acids with a boronate affinity gel. Analytical biochemistry. 1986 Apr; 154(1):71-4. doi: 10.1016/0003-2697(86)90497-5. [PMID: 3706738]
  • J R Crowley, M W Couch, C M Williams, R M Threatte, M J Fregly. Normal excretion of m-hydroxymandelic acid in hypertensive patients. Clinica chimica acta; international journal of clinical chemistry. 1981 Jan; 109(2):125-31. doi: 10.1016/0009-8981(81)90326-0. [PMID: 7471493]
  • V HRUSKA, J DUCHON. [3-METHOXY, 4-HYDROXYMANDELIC ACID IN THE DIAGNOSIS OF PHEOCHROMOCYTOMA]. Casopis lekaru ceskych. 1963 Aug; 102(?):962-7. doi: . [PMID: 14051527]


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