(±)-Furaneol (BioDeep_00000000995)

   

human metabolite PANOMIX_OTCML-2023 blood metabolite


代谢物信息卡片


4-Hydroxy-2,5-dimethyl-3(2H)-furanone, 15 wt. \\% (in propylene glycol), FG

化学式: C6H8O3 (128.0473)
中文名称: 4-羟基-2,5-二甲基-3(2H)呋喃酮, 呋喃酮
谱图信息: 最多检出来源 Viridiplantae(plant) 31.19%

分子结构信息

SMILES: CC1=C(O)C(=O)C(C)O1
InChI: InChI=1S/C6H8O3/c1-3-5(7)6(8)4(2)9-3/h3,8H,1-2H3

描述信息

4-hydroxy-2,5-dimethylfuran-3-one is a member of the class of furans that is 2,5-dimethylfuran carrying additional oxo and hydroxy groups at positions 3 and 4 respectively. It has been found particularly in strawberries and other such fruits. It has a role as a flavouring agent, a fragrance and a plant metabolite. It is a member of furans, an enol and a cyclic ketone. It is a conjugate acid of a 4-hydroxy-2,5-dimethylfuran-3-olate.
Furaneol is a natural product found in Mangifera indica, Fragaria, and other organisms with data available.
Furaneol is a metabolite found in or produced by Saccharomyces cerevisiae.
A member of the class of furans that is 2,5-dimethylfuran carrying additional oxo and hydroxy groups at positions 3 and 4 respectively. It has been found particularly in strawberries and other such fruits.
Flavouring agent. Furaneol is found in many foods, some of which are fruits, nuts, pulses, and cereals and cereal products.
(±)-Furaneol is found in animal foods. (±)-Furaneol is a flavouring agent.
Furaneol is mainly isolated from American grape (Vitis labrusca) and its hybrid grape. Furaneol is an important aroma compound in fruits and contribute to the strawberry-like note in some wines[1].
Furaneol is mainly isolated from American grape (Vitis labrusca) and its hybrid grape. Furaneol is an important aroma compound in fruits and contribute to the strawberry-like note in some wines[1].

同义名列表

51 个代谢物同义名

4-Hydroxy-2,5-dimethyl-3(2H)-furanone, 15 wt. \\% (in propylene glycol), FG; 4-Hydroxy-2,5-dimethyl-3(2H)-furanone, analytical standard; 4-Hydroxy-2,5-dimethyl-3(2H)-furanone, natural, >=98\\%, FG; 4-Hydroxy-2,5-dimethyl-3(2H)-furanone, >=98\\%, FCC, FG; 4-Hydroxy-2,5-dimethyl-3(2H)-furanone, >=99.0\\% (GC); 4-Hydroxy-2,5-dimethyl-3(2H)-furanone (natural); InChI=1/C6H8O3/c1-3-5(7)6(8)4(2)9-3/h3,8H,1-2H; 4-hydroxy-2,5-dimethyl-2,3-dihydrofuran-3-one; 2,3-Dihydro-4-hydroxy-2,5-dimethyl-3-furanone; 4-oxo-3-hydroxy-2,5-dimethyl-4,5-dihydrofuran; 2,5-Dimethyl-4-hydroxy-2,3-dihydrofuran-3-one; 2,5-Dimethyl-3-hydroxy-4-oxo-4,5-dihydrofuran; 4-HYDROXY-2,5-DIMETHYL-3(2H)-FURANONE [FHFI]; 4-HYDROXY-2,5-DIMETHYL-3(2H)-FURANONE [FCC]; 2,5-Dimethyl-4-hydroxy-3(2H)-furanone-13C2; 3(2H)-Furanone, 4-hydroxy-2,5-dimethyl-; 2,5-dimethyl-4-hydroxy-(2h)-furan-3-one; 2,5-dimethyl-4-hydroxy-3-oxo-(2H)-furan; 3(2H)-FURANONE, 2,5-DIMETHYL-4-HYDROXY-; 2.5-dimethyl-4-hydroxy-3-(2H)-furanone; 2,5-dimethyl-4-hydroxy-3-(2H)-furanone; 4-hydroxy-2,5-dimethyl-furan-3(2H)-one; 2,5-dimethyl-4-hydroxy-3(2H)-furanone; 4-hydroxy-2,5-dimethylfuran-3(2H)-one; 4-hydroxy-2,5-dimethyl-3-oxo-2H-furan; 4-hydroxy-2,5-dimethyl-3(2H)-furanone; 2,5-dimethyl-4-hydroxy-3[2H] furanone; 4-Hydroxy-2,5-dimethylfuran-2(3H)-one; 4-Hydroxy-2,5-dimethyl-3(2H)furanone; 4-hydroxy-2,5-dimethylfuran-3-one; 4-hydroxy-2,5-dimethyl-3-furanone; DIMETHYLHYDROXY FURANONE [INCI]; 2,5-DIMETHYLDIHYDROFURANOLONE; DIMETHYL DIHYDROFURANOLONE; Dimethylhydroxy furanone; dimethylhydroxyfuranone; furaneol, (R)-isomer; furaneol, (S)-isomer; Strawberry furanone; Pineapple ketone; UNII-20PI8YZP7A; (+/-)-Furaneol; (±)-Furaneol; Tox21_300823; 20PI8YZP7A; Furaneol; alletone; ALNOSE; 4-HDMF; HDMF; Furaneol



数据库引用编号

19 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

43 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(43)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

5 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 12 ACE, ACE2, ACLY, CAT, CRYZ, GADD45A, HDC, MITF, POMC, TYR, TYRP1, UMODL1
Peripheral membrane protein 2 GBA1, HSD17B6
Endosome membrane 1 TYRP1
Nucleus 5 GADD45A, HDC, JUND, MITF, MYB
cytosol 8 ACLY, CAT, CRYZ, HDC, LIPE, MITF, MYB, TNFRSF11A
trans-Golgi network 1 GBA1
nucleoplasm 5 ACLY, GADD45A, JUND, MITF, MYB
RNA polymerase II transcription regulator complex 2 JUND, MYB
Cell membrane 4 ACE, ACE2, LIPE, UMODL1
Early endosome membrane 1 HSD17B6
cell surface 2 ACE2, UMODL1
Golgi apparatus 1 GBA1
lysosomal membrane 2 GBA1, MITF
Cytoplasm, cytosol 2 ACLY, LIPE
Lysosome 3 ACE, GBA1, TYR
endosome 1 ACE
plasma membrane 5 ACE, ACE2, IGHE, OR5M3, TNFRSF11A
Membrane 7 ACE, ACE2, ACLY, CAT, HDC, LIPE, MYB
apical plasma membrane 1 ACE2
caveola 1 LIPE
extracellular exosome 6 ACE, ACE2, ACLY, CAT, CRYZ, GBA1
Lysosome membrane 2 GBA1, MITF
Lumenal side 2 GBA1, HSD17B6
endoplasmic reticulum 2 GBA1, HSD17B6
extracellular space 5 ACE, ACE2, IGHE, POMC, UMODL1
lysosomal lumen 1 GBA1
perinuclear region of cytoplasm 1 TYR
mitochondrion 2 CAT, CRYZ
protein-containing complex 2 CAT, MITF
intracellular membrane-bounded organelle 3 CAT, HSD17B6, TYR
Microsome membrane 1 HSD17B6
Single-pass type I membrane protein 7 ACE, ACE2, IGHE, TNFRSF11A, TYR, TYRP1, UMODL1
Secreted 3 ACE, ACE2, POMC
extracellular region 6 ACE, ACE2, ACLY, CAT, IGHE, POMC
mitochondrial matrix 1 CAT
transcription regulator complex 1 JUND
Cell projection, cilium 1 ACE2
external side of plasma membrane 3 ACE, TNFRSF11A, UMODL1
Melanosome membrane 2 TYR, TYRP1
Golgi-associated vesicle 1 TYR
Apical cell membrane 1 ACE2
Membrane raft 2 ACE2, TNFRSF11A
focal adhesion 1 CAT
Peroxisome 1 CAT
intracellular vesicle 1 TYRP1
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
secretory granule 1 POMC
nuclear speck 1 GADD45A
cilium 1 ACE2
chromatin 2 JUND, MITF
IgE immunoglobulin complex 1 IGHE
brush border membrane 2 ACE, ACE2
sperm midpiece 1 ACE
[Isoform 2]: Cell membrane 1 IGHE
Lipid droplet 1 LIPE
Membrane, caveola 1 LIPE
Melanosome 2 TYR, TYRP1
basal plasma membrane 1 ACE
ficolin-1-rich granule lumen 2 ACLY, CAT
secretory granule lumen 2 CAT, POMC
endoplasmic reticulum lumen 1 ACE2
nuclear matrix 1 MYB
transcription repressor complex 1 JUND
endocytic vesicle membrane 1 ACE2
azurophil granule lumen 1 ACLY
clathrin-coated endocytic vesicle membrane 1 TYRP1
[Isoform 1]: Cell membrane 1 TNFRSF11A
[Isoform 3]: Cell membrane 1 IGHE
transcription factor AP-1 complex 1 JUND
[Isoform 1]: Secreted 1 IGHE
IgE B cell receptor complex 1 IGHE
immunoglobulin complex, circulating 1 IGHE
catalase complex 1 CAT
[Angiotensin-converting enzyme, soluble form]: Secreted 1 ACE
[Isoform Testis-specific]: Cell membrane 1 ACE
[Processed angiotensin-converting enzyme 2]: Secreted 1 ACE2
[Isoform 2]: Apical cell membrane 1 ACE2
[Isoform RANK-e5a]: Cell membrane 1 TNFRSF11A


文献列表

  • Dominika Osiecka, Christina Vakh, Patrycja Makoś-Chełstowska, Paweł Kubica. Plant-based meat substitute analysis using microextraction with deep eutectic solvent followed by LC-MS/MS to determine acrylamide, 5-hydroxymethylfurfural and furaneol. Analytical and bioanalytical chemistry. 2024 Feb; 416(5):1117-1126. doi: 10.1007/s00216-023-05107-6. [PMID: 38123751]
  • Issei Yokoyama, Motoko Ohata, Yusuke Komiya, Jun Nagasao, Keizo Arihara. Inhalation of odors containing DMHF generated by the Maillard reaction affects physiological parameters in rats. Scientific reports. 2020 08; 10(1):13931. doi: 10.1038/s41598-020-70843-z. [PMID: 32811855]
  • Suganthi Martena Devadas, Usha Y Nayak, Reema Narayan, Manjunath H Hande, Mamatha Ballal. 2,5-Dimethyl-4-hydroxy-3(2H)-furanone as an Anti-biofilm Agent Against Non-Candida albicans Candida Species. Mycopathologia. 2019 Jun; 184(3):403-411. doi: 10.1007/s11046-019-00341-y. [PMID: 31187338]
  • Yuanyuan Zhang, Xueren Yin, Yuwei Xiao, Zuying Zhang, Shaojia Li, Xiaofen Liu, Bo Zhang, Xiaofang Yang, Donald Grierson, Guihua Jiang, Harry J Klee, Kunsong Chen. An ETHYLENE RESPONSE FACTOR-MYB Transcription Complex Regulates Furaneol Biosynthesis by Activating QUINONE OXIDOREDUCTASE Expression in Strawberry. Plant physiology. 2018 09; 178(1):189-201. doi: 10.1104/pp.18.00598. [PMID: 29987002]
  • Marta Cialiè Rosso, Erica Liberto, Nicola Spigolon, Mauro Fontana, Marco Somenzi, Carlo Bicchi, Chiara Cordero. Evolution of potent odorants within the volatile metabolome of high-quality hazelnuts (Corylus avellana L.): evaluation by comprehensive two-dimensional gas chromatography coupled with mass spectrometry. Analytical and bioanalytical chemistry. 2018 Jun; 410(15):3491-3506. doi: 10.1007/s00216-017-0832-6. [PMID: 29313080]
  • Chuankui Song, Xiaotong Hong, Shuai Zhao, Jingyi Liu, Katja Schulenburg, Fong-Chin Huang, Katrin Franz-Oberdorf, Wilfried Schwab. Glucosylation of 4-Hydroxy-2,5-Dimethyl-3(2H)-Furanone, the Key Strawberry Flavor Compound in Strawberry Fruit. Plant physiology. 2016 05; 171(1):139-51. doi: 10.1104/pp.16.00226. [PMID: 26993618]
  • Kanako Sasaki, Hideki Takase, Hironori Kobayashi, Hironori Matsuo, Ryoji Takata. Molecular cloning and characterization of UDP-glucose: furaneol glucosyltransferase gene from grapevine cultivar Muscat Bailey A (Vitis labrusca × V. vinifera). Journal of experimental botany. 2015 Oct; 66(20):6167-74. doi: 10.1093/jxb/erv335. [PMID: 26160581]
  • André Schiefner, Quirin Sinz, Irmgard Neumaier, Wilfried Schwab, Arne Skerra. Structural basis for the enzymatic formation of the key strawberry flavor compound 4-hydroxy-2,5-dimethyl-3(2H)-furanone. The Journal of biological chemistry. 2013 Jun; 288(23):16815-16826. doi: 10.1074/jbc.m113.453852. [PMID: 23589283]
  • Markus Verginer, Barbara Siegmund, Massimiliano Cardinale, Henry Müller, Young Choi, Carlos B Míguez, Erich Leitner, Gabriele Berg. Monitoring the plant epiphyte Methylobacterium extorquens DSM 21961 by real-time PCR and its influence on the strawberry flavor. FEMS microbiology ecology. 2010 Oct; 74(1):136-45. doi: 10.1111/j.1574-6941.2010.00942.x. [PMID: 20662926]
  • Fernando de la Peña Moreno, Gracia Patricia Blanch, Gema Flores, Maria Luisa Ruiz Del Castillo. Development of a method based on on-line reversed phase liquid chromatography and gas chromatography coupled by means of an adsorption-desorption interface for the analysis of selected chiral volatile compounds in methyl jasmonate treated strawberries. Journal of chromatography. A. 2010 Feb; 1217(7):1083-8. doi: 10.1016/j.chroma.2009.10.037. [PMID: 19878953]
  • Christian Landmann, Barbara Fink, Wilfried Schwab. FaGT2: a multifunctional enzyme from strawberry (Fragaria x ananassa) fruits involved in the metabolism of natural and xenobiotic compounds. Planta. 2007 Jul; 226(2):417-28. doi: 10.1007/s00425-007-0492-4. [PMID: 17323078]
  • Woo Sang Sung, Hyun Jun Jung, Keunnam Park, Hyun Soo Kim, In-Seon Lee, Dong Gun Lee. 2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF); antimicrobial compound with cell cycle arrest in nosocomial pathogens. Life sciences. 2007 Jan; 80(6):586-91. doi: 10.1016/j.lfs.2006.10.008. [PMID: 17097685]
  • Thomas Raab, Juan Antonio López-Ráez, Dorothée Klein, Jose Luis Caballero, Enriqueta Moyano, Wilfried Schwab, Juan Muñoz-Blanco. FaQR, required for the biosynthesis of the strawberry flavor compound 4-hydroxy-2,5-dimethyl-3(2H)-furanone, encodes an enone oxidoreductase. The Plant cell. 2006 Apr; 18(4):1023-37. doi: 10.1105/tpc.105.039784. [PMID: 16517758]
  • Yukiko Tokitomo, Martin Steinhaus, Andrea Büttner, Peter Schieberle. Odor-active constituents in fresh pineapple (Ananas comosus [L.] Merr.) by quantitative and sensory evaluation. Bioscience, biotechnology, and biochemistry. 2005 Jul; 69(7):1323-30. doi: 10.1271/bbb.69.1323. [PMID: 16041138]
  • Thomas Raab, Tobias Hauck, Anja Knecht, Ulrich Schmitt, Ulrike Holzgrabe, Wilfried Schwab. Tautomerism of 4-hydroxy-2,5-dimethyl-3(2H)-furanone: evidence for its enantioselective biosynthesis. Chirality. 2003 Aug; 15(7):573-8. doi: 10.1002/chir.10247. [PMID: 12840820]
  • Martina Wein, Noa Lavid, Stefan Lunkenbein, Efraim Lewinsohn, Wilfried Schwab, Ralf Kaldenhoff. Isolation, cloning and expression of a multifunctional O-methyltransferase capable of forming 2,5-dimethyl-4-methoxy-3(2H)-furanone, one of the key aroma compounds in strawberry fruits. The Plant journal : for cell and molecular biology. 2002 Sep; 31(6):755-65. doi: 10.1046/j.1365-313x.2002.01396.x. [PMID: 12220266]
  • Louise Urruty, Jean-Luc Giraudel, Sovan Lek, Philippe Roudeillac, Michel Montury. Assessment of strawberry aroma through SPME/GC and ANN methods. Classification and discrimination of varieties. Journal of agricultural and food chemistry. 2002 May; 50(11):3129-36. doi: 10.1021/jf0116799. [PMID: 12009974]
  • H Mi, K Hiramoto, K Kujirai, K Ando, Y Ikarashi, K Kikugawa. Effect of food reductones, 2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF) and hydroxyhydroquinone (HHQ), on lipid peroxidation and type IV and I allergy responses of mouse. Journal of agricultural and food chemistry. 2001 Oct; 49(10):4950-5. doi: 10.1021/jf010556l. [PMID: 11600049]
  • R G Buttery, G R Takeoka, M Naim, H Rabinowitch, Y Nam. Analysis of Furaneol in tomato using dynamic headspace sampling with sodium sulfate. Journal of agricultural and food chemistry. 2001 Sep; 49(9):4349-51. doi: 10.1021/jf0105236. [PMID: 11559136]
  • T Sasaki, J Yamakoshi, M Saito, K Kasai, T Matsudo, T Koga, K Mori. Antioxidative activities of 4-hydroxy-3(2H)-furanones and their anti-cataract effect on spontaneous cataract rat (ICR/f). Bioscience, biotechnology, and biochemistry. 1998 Oct; 62(10):1865-9. doi: 10.1271/bbb.62.1865. [PMID: 9836421]
  • K Hiramoto, T Kato, Y Takahashi, K Yugi, K Kikugawa. Absorption and induction of micronucleated peripheral reticulocytes in mice after oral administration of fragrant hydroxyfuranones generated in the Maillard reaction. Mutation research. 1998 Jul; 415(1-2):79-83. doi: 10.1016/s1383-5718(98)00059-x. [PMID: 9711264]
  • R Roscher, H Koch, M Herderich, P Schreier, W Schwab. Identification of 2,5-dimethyl-4-hydroxy-3[2H]-furanone beta-D-glucuronide as the major metabolite of a strawberry flavour constituent in humans. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 1997 Aug; 35(8):777-82. doi: 10.1016/s0278-6915(97)00055-0. [PMID: 9350222]