Propyl gallate (BioDeep_00000230867)

 

Secondary id: BioDeep_00000002172, BioDeep_00000229802, BioDeep_00000412936

human metabolite PANOMIX_OTCML-2023 natural product


代谢物信息卡片


Propyl gallate, Pharmaceutical Secondary Standard; Certified Reference Material

化学式: C10H12O5 (212.0685)
中文名称: 没食子酸丙酯
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 27.63%

分子结构信息

SMILES: CCCOC(=O)C1=CC(=C(C(=C1)O)O)O
InChI: InChI=1S/C10H12O5/c1-2-3-15-10(14)6-4-7(11)9(13)8(12)5-6/h4-5,11-13H,2-3H2,1H3

描述信息

Propyl gallate appears as fine white to creamy-white crystalline powder. Odorless or with a faint odor. Melting point 150 °C. Insoluble in water. Slightly bitter taste.
N-propyl gallate is a trihydroxybenzoic acid.
Propyl Gallate is under investigation in clinical trial NCT01450098 (A Study of LY2484595 in Healthy Subjects).
Propyl gallate is a natural product found in Alchornea glandulosa, Mangifera indica, and Zea mays with data available.
Propyl gallate is found in corn. Propyl gallate is an antioxidant used in foods especially animal fats and vegetable oils. Synergistic with other antioxidants such as Butylated hydroxyanisole DNB28-K and 2,6-Di-tert-butyl-4-methylphenol HCH42-H. Especially effective with polyunsaturated fats. Indirect food additive arising from paper or board packaging, adhesives and food contact polymers Propyl gallate is an anti-oxidant. It protects against oxidation by hydrogen peroxide and oxygen free radicals, in a catalytic manner similar to superoxide dismutase. Propyl gallate, or propyl 3,4,5-trihydroxybenzoate is an ester formed by the condensation of gallic acid and propanol. It is an antioxidant added to foods containing oils and fats to prevent oxidation.[citation needed] As a food additive, it is used under the E number E310.Propyl gallate has been shown to exhibit pro-oxidant and radical scavenger functions (A7908, A7909).
Antioxidant for foods, fats, oils, ethers, emulsions, waxes, and transformer oils.
Propyl gallate is found in corn. Propyl gallate is an antioxidant used in foods especially animal fats and vegetable oils. Synergistic with other antioxidants such as Butylated hydroxyanisole DNB28-K and 2,6-Di-tert-butyl-4-methylphenol HCH42-H. Especially effective with polyunsaturated fats. Indirect food additive arising from paper or board packaging, adhesives and food contact polymers Propyl gallate is an anti-oxidant. It protects against oxidation by hydrogen peroxide and oxygen free radicals, in a catalytic manner similar to superoxide dismutase. Propyl gallate, or propyl 3,4,5-trihydroxybenzoate is an ester formed by the condensation of gallic acid and propanol. It is an antioxidant added to foods containing oils and fats to prevent oxidation.[citation needed] As a food additive, it is used under the E number E310
Antioxidant used in foods especies animal fats and vegetable oils. Synergistic with other antioxidants such as Butylated hydroxyanisole DNB28-K and 2,6-Di-tert-butyl-4-methylphenol HCH42-H. Especies effective with polyunsaturated fats. Indirect food additive arising from paper or board packaging, adhesives and food contact polymers
D020011 - Protective Agents > D000975 - Antioxidants
Propyl gallate is a common food antioxidant. Propyl gallate can inhibit the production of acrolein, glyoxal and methylglyoxal[1][2].
Propyl gallate is a common food antioxidant. Propyl gallate can inhibit the production of acrolein, glyoxal and methylglyoxal[1][2].

同义名列表

82 个代谢物同义名

Propyl gallate, Pharmaceutical Secondary Standard; Certified Reference Material; InChI=1/C10H12O5/c1-2-3-15-10(14)6-4-7(11)9(13)8(12)5-6/h4-5,11-13H,2-3H2,1H; Propyl gallate, United States Pharmacopeia (USP) Reference Standard; Propyl gallate, European Pharmacopoeia (EP) Reference Standard; N-PROPYL ESTER OF 3,4,5- TRIHYDROXYBENZOIC ACID; Propyl gallate, for microscopy, >=98.0\\% (HPLC); n-Propyl ester of 3,4,5-trihydroxybenzoic acid; Benzoic acid, 3,4,5-trihydroxy-, propyl ester; n-Propyl ester of 3,5-trihydroxybenzoic acid; Propyl gallate, antioxidant, >=98.0\\% (HPLC); 3,4,5-Trihydroxybenzoic acid n-propyl ester; 3,4,5-Trihydroxybenzene-1-propylcarboxylate; 3,4,5-Trihydroxy-benzoic acid propyl ester; Benzoic acid,4,5-trihydroxy-, propyl ester; 3,4,5-Trihydroxybenzoic acid, propyl ester; 3,5-Trihydroxybenzene-1-propylcarboxylate; 3,4,5-Trihydroxybenzoic acid propyl ester; 3,5-Trihydroxybenzoic acid, propyl ester; 5-Methyl-4,5-dihydrothiazole-2-thiol; Propylester kyseliny gallove [Czech]; EFFF5FFA-651C-4DE3-A25F-D807C65D5537; 3,4,5-Trihydroxy-benzoic acid propy; n-Propyl 3,4,5-trihydroxybenzoate; Propyl gallate, USP, 98.0-102.0\\%; n-Propyl-3,4,5-Trihydroxybenzoate; n-Propyl 3,5-trihydroxybenzoate; Propyl 3,4,5-trihydroxybenzoate; Propyl 3,5-trihydroxybenzoate; PROPYL GALLATE [EP MONOGRAPH]; Propylester kyseliny gallove; Propyl gallate, >=98\\%, FCC; Gallic acid, n-propyl ester; Gallic acid n-propyl ester; Gallic acid, propyl ester; Gallic acid propyl esterZ; Gallic acid propyl ester; Gallic acid-propyl ester; PROPYL GALLATE [WHO-DD]; PROPYL GALLATE [USP-RS]; PROPYL GALLATE [VANDF]; PROPYL GALLATE [MART.]; Propyl gallate, powder; PROPYL GALLATE [INCI]; PROPYL GALLATE [HSDB]; PROPYL GALLATE [FHFI]; Propyl gallate, 98\\%; PROPYL GALLATE [FCC]; N-Propyl gallic acid; Propyl gallate [NF]; PROPYL GALLATE [II]; PROPYL GALLATE [MI]; Propyl gallate (NF); Propyl gallic acid; WLN: QR BQ CQ EVO3; Propyl Gallate, NF; Propylgallate,(S); N-Propyl gallate; n-propyl-gallate; Gallate, Propyl; UNII-8D4SNN7V92; Propyl galiate; Propyl gallate; Oprea1_580415; Tox21_202286; Nipagallin P; Tox21_113531; Pro gallin P; Tox21_300060; NCI60_002094; Nipanox S 1; Progallin P; 8D4SNN7V92; Sustane PG; FEMA 2947; AI3-17136; Tenox PG; NIPA 49; l ester; Propyl; e310; PG; n-Propyl gallate



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(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

22 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 AIMP2, ANXA5, BCL2, CASP3, CASP8, CAT, HPGDS, MAPK8, NOS3, PRKX, PTGS2, XDH
Peripheral membrane protein 2 ANXA5, PTGS2
Endoplasmic reticulum membrane 5 BCL2, CALU, CYP1A2, HMOX1, PTGS2
Nucleus 9 AIMP2, BCL2, CASP3, CASP8, HMOX1, MAPK8, NOS3, PARP1, PRKX
cytosol 13 AIMP2, ANXA5, BCL2, CASP3, CASP8, CAT, HMOX1, HPGDS, LIPE, MAPK8, NOS3, PARP1, XDH
nuclear body 1 PARP1
nucleoplasm 8 CASP3, CASP8, HMOX1, HPGDS, MAPK8, NOS3, PARP1, PRKX
Cell membrane 3 LIPE, SELP, TNF
Cytoplasmic side 1 HMOX1
lamellipodium 1 CASP8
Synapse 1 MAPK8
cell surface 1 TNF
glutamatergic synapse 1 CASP3
Golgi apparatus 2 CALU, NOS3
Golgi membrane 1 NOS3
neuronal cell body 2 CASP3, TNF
sarcolemma 1 ANXA5
Cytoplasm, cytosol 3 AIMP2, LIPE, PARP1
plasma membrane 4 F2, NOS3, SELP, TNF
Membrane 8 AIMP2, ANXA5, BCL2, CALU, CAT, HMOX1, LIPE, PARP1
axon 1 MAPK8
caveola 3 LIPE, NOS3, PTGS2
extracellular exosome 4 ANXA5, CAT, F2, SELP
endoplasmic reticulum 4 BCL2, CALU, HMOX1, PTGS2
extracellular space 5 F2, HMOX1, SELP, TNF, XDH
perinuclear region of cytoplasm 2 HMOX1, NOS3
mitochondrion 4 BCL2, CASP8, CAT, PARP1
protein-containing complex 5 BCL2, CASP8, CAT, PARP1, PTGS2
intracellular membrane-bounded organelle 3 CAT, CYP1A2, HPGDS
Microsome membrane 2 CYP1A2, PTGS2
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 SELP
Secreted 3 CALU, F2, SELP
extracellular region 6 ANXA5, CALU, CAT, F2, SELP, TNF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 3 BCL2, CASP8, HMOX1
mitochondrial matrix 1 CAT
transcription regulator complex 1 PARP1
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 3 ANXA5, SELP, TNF
nucleolus 1 PARP1
Cytoplasm, P-body 1 NOS3
P-body 1 NOS3
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Cell projection, lamellipodium 1 CASP8
Membrane raft 1 TNF
pore complex 1 BCL2
focal adhesion 2 ANXA5, CAT
Peroxisome 2 CAT, XDH
sarcoplasmic reticulum 1 XDH
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 2 ANXA5, F2
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Zymogen granule membrane 1 ANXA5
neuron projection 1 PTGS2
chromatin 1 PARP1
phagocytic cup 1 TNF
Chromosome 1 PARP1
cytoskeleton 2 CASP8, NOS3
Nucleus, nucleolus 1 PARP1
nuclear replication fork 1 PARP1
chromosome, telomeric region 1 PARP1
blood microparticle 1 F2
site of double-strand break 1 PARP1
nuclear envelope 1 PARP1
Lipid droplet 1 LIPE
Membrane, caveola 1 LIPE
Melanosome 1 CALU
Cytoplasm, Stress granule 1 NOS3
cytoplasmic stress granule 1 NOS3
cell body 1 CASP8
myelin sheath 1 BCL2
platelet dense granule membrane 1 SELP
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 1 CAT
Golgi lumen 1 F2
endoplasmic reticulum lumen 3 CALU, F2, PTGS2
endocytic vesicle membrane 1 NOS3
Single-pass type IV membrane protein 1 HMOX1
vesicle membrane 1 ANXA5
Sarcoplasmic reticulum lumen 1 CALU
protein-DNA complex 1 PARP1
basal dendrite 1 MAPK8
CD95 death-inducing signaling complex 1 CASP8
death-inducing signaling complex 2 CASP3, CASP8
ripoptosome 1 CASP8
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
platelet alpha granule membrane 1 SELP
site of DNA damage 1 PARP1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
platelet dense granule lumen 1 SELP
catalase complex 1 CAT
endothelial microparticle 1 ANXA5
[Poly [ADP-ribose] polymerase 1, processed N-terminus]: Chromosome 1 PARP1
[Poly [ADP-ribose] polymerase 1, processed C-terminus]: Cytoplasm 1 PARP1
BAD-BCL-2 complex 1 BCL2
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Tianyuan Li, Tin Shen, Kai Shi, Yunfeng Zhang. Transcriptome analysis reveals the effect of propyl gallate on kiwifruit callus formation. Plant cell reports. 2024 Feb; 43(3):60. doi: 10.1007/s00299-024-03140-y. [PMID: 38334781]
  • Priyanka Raju Chougule, Rajendra Sangaraju, Pradeep B Patil, S S Y H Qadri, Virendra V Panpatil, Sudip Ghosh, Sathish Kumar Mungamuri, Manjula Bhanoori, Sukesh Narayan Sinha. Effect of ethyl gallate and propyl gallate on dextran sulfate sodium (DSS)-induced ulcerative colitis in C57BL/6 J mice: preventive and protective. Inflammopharmacology. 2023 Jun; ?(?):. doi: 10.1007/s10787-023-01254-5. [PMID: 37266812]
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  • Siyu Zhang, Joseph R Hyatt, Casimir C Akoh. Solvent-free enzymatic synthesis of 1,2-dipalmitoylgalloylglycerol: Characterization and optimization of reaction condition. Food chemistry. 2021 May; 344(?):128604. doi: 10.1016/j.foodchem.2020.128604. [PMID: 33243556]
  • Corinne Vanucci-Bacqué, Florence Bedos-Belval. Anti-inflammatory activity of naturally occuring diarylheptanoids - A review. Bioorganic & medicinal chemistry. 2021 02; 31(?):115971. doi: 10.1016/j.bmc.2020.115971. [PMID: 33422907]
  • Siyu Zhang, Sarah A Willett, Joseph R Hyatt, Silvana Martini, Casimir C Akoh. Phenolic compounds as antioxidants to improve oxidative stability of menhaden oil-based structured lipid as butterfat analog. Food chemistry. 2021 Jan; 334(?):127584. doi: 10.1016/j.foodchem.2020.127584. [PMID: 32711274]
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  • Dong Liu, Yuemin Pan, Kunyuan Li, Dandan Li, Ping Li, Zhimou Gao. Proteomics Reveals the Mechanism Underlying the Inhibition of Phytophthora sojae by Propyl Gallate. Journal of agricultural and food chemistry. 2020 Aug; 68(31):8151-8162. doi: 10.1021/acs.jafc.0c02371. [PMID: 32633954]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Pascual García-Pérez, Sonia Losada-Barreiro, Pedro P Gallego, Carlos Bravo-Díaz. Adsorption of gallic acid, propyl gallate and polyphenols from Bryophyllum extracts on activated carbon. Scientific reports. 2019 10; 9(1):14830. doi: 10.1038/s41598-019-51322-6. [PMID: 31616022]
  • Alireza Einali. The induction of salt stress tolerance by propyl gallate treatment in green microalga Dunaliella bardawil, through enhancing ascorbate pool and antioxidant enzymes activity. Protoplasma. 2018 Mar; 255(2):601-611. doi: 10.1007/s00709-017-1173-1. [PMID: 28990124]
  • Małgorzata Sztanke, Krzysztof Sztanke. Biologically important hydrazide-containing fused azaisocytosines as antioxidant agents. Redox report : communications in free radical research. 2017 Nov; 22(6):572-581. doi: 10.1080/13510002.2017.1364330. [PMID: 28812524]
  • Yifen Lin, Yixiong Lin, Hetong Lin, John Shi, Yihui Chen, Hui Wang. Inhibitory effects of propyl gallate on membrane lipids metabolism and its relation to increasing storability of harvested longan fruit. Food chemistry. 2017 Feb; 217(?):133-138. doi: 10.1016/j.foodchem.2016.08.065. [PMID: 27664618]
  • Qunqun Wang, Kai Zhou, Yong Ning, Guanghua Zhao. Effect of the structure of gallic acid and its derivatives on their interaction with plant ferritin. Food chemistry. 2016 Dec; 213(?):260-267. doi: 10.1016/j.foodchem.2016.06.085. [PMID: 27451180]
  • Jae-Min Kim, Seung-Hyun Choi, Gi-Hae Shin, Jin-Ha Lee, Seong-Ran Kang, Kyun-Young Lee, Ho-Soo Lim, Tae Seok Kang, Ok-Hwan Lee. Method validation and measurement uncertainty for the simultaneous determination of synthetic phenolic antioxidants in edible oils commonly consumed in Korea. Food chemistry. 2016 Dec; 213(?):19-25. doi: 10.1016/j.foodchem.2016.06.053. [PMID: 27451150]
  • Farzaneh Fathi, Jafar Ezzati Nazhad Dolatanbadi, Mohammad-Reza Rashidi, Yadollah Omidi. Kinetic studies of bovine serum albumin interaction with PG and TBHQ using surface plasmon resonance. International journal of biological macromolecules. 2016 Oct; 91(?):1045-50. doi: 10.1016/j.ijbiomac.2016.06.054. [PMID: 27327906]
  • Jeung-Eun Lee, Jung-Min Kim, Hyun-Jun Jang, Se-Young Lim, Seon-Jeong Choi, Nan-Hee Lee, Pann-Ghill Suh, Ung-Kyu Choi. Propyl gallate inhibits adipogenesis by stimulating extracellular signal-related kinases in human adipose tissue-derived mesenchymal stem cells. Molecules and cells. 2015 Apr; 38(4):336-42. doi: 10.14348/molcells.2015.2238. [PMID: 25813451]
  • Lu Ma, Xiao-fa Zhu, Yu-yun Wu, Ke-ji Chen, Da-zhuo Shi, Hui-jun Yin. Protective effect of propyl gallate against oxidized low-density lipoprotein-induced injury of endothelial cells. Chinese journal of integrative medicine. 2015 Apr; 21(4):299-306. doi: 10.1007/s11655-014-1980-6. [PMID: 25588940]
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  • Sonia Losada-Barreiro, Verónica Sánchez-Paz, Carlos Bravo-Díaz. Effects of emulsifier hydrophile-lipophile balance and emulsifier concentration on the distributions of gallic acid, propyl gallate, and α-tocopherol in corn oil emulsions. Journal of colloid and interface science. 2013 Jan; 389(1):1-9. doi: 10.1016/j.jcis.2012.07.036. [PMID: 22939258]
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