(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid

• ChemBase ID: 6195
• Molecular Formular: C11H12O5
• Molecular Mass: 224.20998
• Monoisotopic Mass: 224.06847348
• SMILES: c1(c(cc(cc1OC)/C=C/C(=O)O)OC)O
• Canonical SMILES: COc1cc(/C=C/C(=O)O)cc(c1O)OC
• InChI: InChI=1S/C11H12O5/c1-15-8-5-7(3-4-10(12)13)6-9(16-2)11(8)14/h3-6,14H,1-2H3,(H,12,13)/b4-3+
• InChIKey: PCMORTLOPMLEFB-ONEGZZNKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid; 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid
• IUPAC Traditional name: sinapinic acid; sinapoyl alcohol; 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid
• Synonyms: SINAPINATE; 3,5-DIMETHOXY-4-HYDROXY CINNAMIC ACID; Sinapic acid; Sinapinic acid; Sinapic acid; 4-Hydroxy-3,5-dimethoxycinnamic acid; 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid; 3,5-Dimethoxy-4-hydroxycinnamic acid; Sinapinic acid; 4-Hydroxy-3,5-dimethoxy-cinnamic acid; Sinapinic acid; trans-4-Hydroxy-3,5-dimethoxy-cinnamic acid; trans-Sinapinic acid; trans-Sinapic acid; 3,5-Dimethoxy-4-hydroxycinnamic acid; 3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic Acid; NSC 59261; Synapitic Acid; Sinapic Acid; 3,5-二甲氧基-4-羟基肉桂酸; 4-羟基-3,5-二甲氧基肉桂酸; 白芥酸; 芥子酸; 芥子酸; 白芥酸; 3,5-二甲氧基-4-羟基肉桂酸

Database IDs

• CAS Number: 530-59-6; 7362-37-0
• EC Number: 208-487-3
• MDL Number: MFCD00004401
• Beilstein Number: 2699118; 2130006
• PubChem SID: 24888356; 160969620; 24894171; 24872946
• PubChem CID: 637775
• CHEBI ID: 15714
• CHEMBL: 109341
• Chemspider ID: 553361
• DrugBank ID: DB08587
• Wikipedia Title: Sinapinic_acid

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.6066942
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.37177408
• LogD (pH = 7.4): -1.8277447
• Log P: 1.5171784
• Molar Refractivity: 57.9672 cm^3
• Polarizability: 21.899372 Å^3
• Polar Surface Area: 75.99 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.63
• LOG S: -2.55
• Solubility (Water): 6.31e-01 g/l

PROPERTIES

Physical Property

• Solubility: H2O: slightly soluble; methanol: water: soluble; polar organic solvents: soluble
• Apperance: faintly yellow; slightly yellow; white powder
• Melting Point: ~202 °C; 188 - 190°C; 195-205 °C (dec.); 203–205 °C (decomposes); 203-205(dec.)°C; ca 195°C dec.
• Hydrophobicity(logP): 1.204

Safety Information

• Storage Warning: Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98%; ≥99.0% (HPLC); ≥99.0% (T); ≥99.5%; ≥99.5% (HPLC); 95%; 98%
• Grade: analytical standard; matrix substance for MALDI-MS; puriss. p.a.
• Suitability: in accordance for UV test
• Cation Traces: Al: ≤1 mg/kg; Ba: ≤1 mg/kg; Ba: ≤5 mg/kg; Ca: ≤10 mg/kg; Ca: ≤2 mg/kg; Cd: ≤1 mg/kg; Cd: ≤5 mg/kg; Co: ≤1 mg/kg; Co: ≤5 mg/kg; Cr: ≤1 mg/kg; Cr: ≤5 mg/kg; Cu: ≤1 mg/kg; Cu: ≤5 mg/kg; Fe: ≤1 mg/kg; Fe: ≤20 mg/kg; K: ≤2 mg/kg; K: ≤50 mg/kg; Li: ≤1 mg/kg; Mg: ≤1 mg/kg; Mg: ≤5 mg/kg; Mn: ≤1 mg/kg; Mn: ≤5 mg/kg; Na: ≤2 mg/kg; Na: ≤50 mg/kg; Ni: ≤1 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Sr: ≤1 mg/kg; Zn: ≤1 mg/kg; Zn: ≤5 mg/kg
• Shelf Life: (limited shelf life, expiry date on the label)
• Mol. Weight: monoisotopic mol wt 224.06839 Da
• Analyte suitability: dendrimers; fullerenes; peptides; proteins
• Empirical Formula (Hill Notation): C11H12O5
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 05203038

MP Biomedicals Rare Chemical collection

DrugBank - DB08587

Drug information: experimental

Sigma Aldrich - S8313

Application
Matrix for protein MALDI-MS
Linkage
Also available as part of MALDI calibration kits MS-CAL1 and MS-CAL3.

Sigma Aldrich - D7927

包装
1, 5 g in poly bottle

Sigma Aldrich - 85429

Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 85429.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - S486800

Sinapic acid is a small naturally occurring hydroxycinnamic acid. Sinapic Acid is a member of the phenylpropanoid family. It is a useful matrix for a wide variety of peptides and proteins. It serves well as a matrix for MALDI due to its ability to absorb

REFERENCES

• Tzagoloff, A., et al.: Plant Physiology, 38, 202 (1963)
• Bunzel M., et al.: J. Agric. Food Chem., 51, 1427 (1963)
• Karvela, E., et al.: Food Chem., 110, 263 (1963)