Basic information
- CAS
99-24-1- Standard SMILES
COC(=O)c1cc(O)c(O)c(O)c1- InChIKey
FBSFWRHWHYMIOG-UHFFFAOYSA-N- Molecular formula
- C8H8O5
- Average molar mass
- 184.15 g/mol
- Monoisotopic mass
- 184.03717335
Names & identifiers
- Preferred name
- Methyl Gallate
- IUPAC
- methyl 3,4,5-trihydroxybenzoate
- English name
- Methyl gallate
- Molecular formula
- C8H8O5
- Molecular weight
- 184.15
Names & synonyms
METHYL GALLATEMethyl 3,4,5-trihydroxybenzoate99-24-1Gallic acid methyl esterMethylgallateBenzoic acid, 3,4,5-trihydroxy-, methyl esterGallic acid, methyl esterDTXSID3059189623D3XG80CNSC-363001CHEBI:145828RefChem:42732
Show more names
methyl galloateNSC 363001AKOS 217-13METHYGALLATEMethylGallate>
DTXCID8049098202-741-7GallicinMFCD000021943,4,5-Trihydroxybenzoic acid methyl esterAI3-00861GALLINCINCHEMBL65675
Database identifiers
- CAS
99-24-1- PubChem CID
- 7428
- DTXSID
DTXSID3059189- ChEMBL
CHEMBL65675- ChEBI
CHEBI:145828- UNII
- 623D3XG80C
- EC Number
- 202-741-7
- Nikkaji
- J4.967K
Properties
Computed structural properties
- XLogP
- 0.9
- Topological polar surface area
- 87 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 181
Experimental & physicochemical properties
Vapor Pressure0.00000178 [mmHg]
Physical DescriptionSolid; [Merck Index] Beige powder; [Sigma-Aldrich MSDS]
Physicochemical properties
- Melting point
- 201 · 201-204 °C
- Boiling point
- 278.08 °C · 278.08°C (rough estimate)
- Density
- 1.384 · 1.3840 (rough estimate)
- refractive index
- 1.569 · 1.5690 (estimate)
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- 50 mg/mL, · ethanol: 50 mg/mL, clear
- form
- Crystalline Powder
- pka
- 8.04 · 8.04±0.23(Predicted)
- color
- White to slightly beige
- Water Solubility
- SOLUBLE IN HOT WATER
- Merck
- 14 · 14,4345
- BRN
- 2113180 · 2113180
- InChI
- 1S/C8H8O5/c1-13-8(12)4-2-5(9)7(11)6(10)3-4/h2-3,9-11H,1H3
- InChIKey
- FBSFWRHWHYMIOG-UHFFFAOYSA-N
- SMILES
- COC(=O)c1cc(O)c(O)c(O)c1
- LogP
- 0.86 · 0.860
- CAS DataBase Reference
- 99 · 99-24-1(CAS DataBase Reference)
- FDA UNII
- 623 D3XG80C · 623D3XG80C
- EPA Substance Registry System
- 3 · Benzoic acid, 3,4,5-trihydroxy-, methyl ester (99-24-1)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 301 · P301+P312+P330-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- Hazard Codes
- Xn,Xi
- Risk Statements
- 22 · 22-36/37/38-43
- Safety Statements
- 26 · 26-36/37-24/25
- WGK Germany
- 3 · 3
- RTECS
- 8000000 · LW8000000
- TSCA
- TSCA listed
- HS Code
- 29182900 · 29182900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 OralEye · Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]；H315 (98%): Causes skin irritation [Warning Skin corrosion/irritation]；H317 (81.6%): May cause an allergic skin reaction [Warning Sensitization, Skin]；H319 (98%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (93.9%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 49 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Regulatory InformationChemical: Benzoic acid, 3,4,5-trihydroxy-, methyl ester
Hazards Summary
Causes delayed allergic hypersensitivity (multiple organ involvement) in 9-day intermittent dermal studies of guinea pigs; [RTECS] Has both immunosuppressive and phytogenic antineoplastic activities; isolated from Acer saccharinum. [ChemIDplus] A skin and strong eye irritant; May cause skin sensitization; Harmful by ingestion; [Sigma-Aldrich MSDS] Search for (99-24-1[EC/RN Number]) AND (allergic OR dermatitis OR sensitizer OR sensitization): no results that it is a skin sensitizer; [PubMed]
Hazard Classes and CategoriesAcute Tox. 4 (100%)；Skin Irrit. 2 (98%)；Skin Sens. 1 (81.6%)；Eye Irrit. 2A (98%)；STOT SE 3 (93.9%)
Regulatory information
Regulatory InformationChemical: Benzoic acid, 3,4,5-trihydroxy-, methyl ester
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- LW8000000
- hs_code
- 29182900
- risk_code
- 22-36/37/38-43
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,Xi
- safety_code
- 26-36/37-24/25
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H302-H315-H319-H335
- Hazard Classifications
- Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P301+P312+P330-P302+P352-P305+P351+P338
Chemistry & industry
Uses & manufacturing
UsesUsed as an antioxidant; [Merck Index]
General Manufacturing InformationBenzoic acid, 3,4,5-trihydroxy-, methyl ester: ACTIVE
Applications
DescriptionMethyl gallate is a phenolic compound found in Terminalia myriocarpa and Geranium niveum. It is also found in wine. It is the methyl ester of gallic acid.
DescriptionMethyl gallate is a phenol that has been found in Meliaceae and has diverse biological activities. It reduces adipogenic hormonal stimulation-induced lipid accumulation in 3T3-L1 cells when used at a concentration of 50 μM. Methyl gallate is active against V. cholerae in vitro (MIC = 32 μg/ml) and reduces V. cholerae-induced intestinal fluid accumulation in suckling mice when administered at doses of 50, 100, and 200 mg/kg. It reduces tumor growth and decreases the number of intratumor CD25+Foxp3high regulatory T cells (Tregs) in an EL-4 model of murine lymphoma. Methyl gallate (0.7, 7, and 70 mg/kg) reduces knee joint edema and leukocyte, neutrophil, and mononuclear cell infiltration in a mouse model of zymosan-induced arthritis.
UsesMethyl gallate exhibits potent antitumor activities by inhibiting tumor infiltration of CD4+CD25+ regulatory T cells.
UsesMethyl 3,4,5-trihydroxybenzoate exhibits potent antitumor activities by inhibiting tumor infiltration of CD4+CD25+ regulatory T cells.
UsesThe gallate ester methyl gallate is used as an antioxidant. A ease was reported using a reprography paper.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
上海赫文斯化工有限公司15721252604 17321035817 · [email protected]
韶远科技（上海）有限公司021-50795510 4000665055 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
Syntechem Co.,Ltd[email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
阿法埃莎（中国）化学有限公司400-6106006 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海诗丹德标准技术服务有限公司021-021-57127007-6622-6622 17621252073 · [email protected]
成都普思生物科技股份有限公司028-85370565-229 18080489829 · [email protected]
成都普菲德生物技术有限公司028-82610909 13388174823 · [email protected]
上海相辉医药科技有限公司13761987713 · [email protected]
合肥天健化工有限公司551-65418679 15856988503;15837135945 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
玛雅试剂+86 (573) 82222445 (0)18006601000 452520369 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
湖南汇百侍生物科技有限公司0731-85526065 13308475853 · [email protected]
斯百全化学（上海）有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
上海源叶生物科技有限公司13636370518 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
赛默飞世尔科技（中国）有限公司800-810-5118 · [email protected]
北京伊诺凯科技有限公司400-810-7969 010-59572699 · [email protected]
南京诺利斯医药科技有限公司13901585132 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
深圳康特腾科技有限公司86-0755-86635001 · [email protected]
北京环宇世纪化学科技有限公司hysj_bj.com
上海湄水化工科技有限公司021-60549325 18616193163
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
日照力德士化工有限公司010-51268198 · [email protected]
美岚实业（上海）有限公司021-58958189 · [email protected]
上海爱蝶实业有限公司021-58957966 18930537195 · [email protected]
成都零六生物科技有限公司400-1166-196 13458535857 · [email protected]
广拓化学（上海）有限公司021-60899189-8001 18918189673 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
上海卓因生物科技有限公司021-61317773 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
Additional notes
DefinitionChEBI: Methyl 3,4,5-trihydroxybenzoate is a gallate ester obtained by the formal condensation of gallic acid with methanol. It exhibits anti-oxidant, anti-tumor, anti-microbial and anti-inflammatory properties. It has a role as a plant metabolite, an anti-inflammatory agent and an antioxidant.
Related reactions
55 records
Compound notes
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