Cas no 845883-03-6 (2-Propenoic acid,3-(3,4-dihydroxyphenyl)-, 1-methylethyl ester, (2E)-)

2-Propenoic acid,3-(3,4-dihydroxyphenyl)-, 1-methylethyl ester, (2E)- structure
845883-03-6 structure
Product Name:2-Propenoic acid,3-(3,4-dihydroxyphenyl)-, 1-methylethyl ester, (2E)-
CAS No:845883-03-6
MF:C12H14O4
MW:222.237164020538
CID:716384
PubChem ID:10013799
Update Time:2024-03-01

2-Propenoic acid,3-(3,4-dihydroxyphenyl)-, 1-methylethyl ester, (2E)- Chemical and Physical Properties

Names and Identifiers

    • 2-Propenoic acid,3-(3,4-dihydroxyphenyl)-, 1-methylethyl ester, (2E)-
    • E-Caffeic acid isoprpyl ester
    • 1-Methylethyl (2E)-3-(3,4-dihydroxyphenyl)-2-propenoate (ACI)
    • (E)-Isopropyl 3-(3,4-dihydroxyphenyl)acrylate
    • Inchi： 1S/C12H14O4/c1-8(2)16-12(15)6-4-9-3-5-10(13)11(14)7-9/h3-8,13-14H,1-2H3/b6-4+
    • InChI Key： HUBVPNVELDTWJF-GQCTYLIASA-N
    • SMILES： C(/C1C=CC(O)=C(O)C=1)=C\C(=O)OC(C)C

Computed Properties

  • Exact Mass: 222.08900
  • Monoisotopic Mass: 222.089
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 4
  • Complexity: 260
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2.3
  • Topological Polar Surface Area: 66.8A^2

Experimental Properties

  • PSA: 66.76000
  • LogP: 2.06260

2-Propenoic acid,3-(3,4-dihydroxyphenyl)-, 1-methylethyl ester, (2E)- Production Method

Production Method 1

Reaction Conditions
1.1 Solvents: Toluene ;  rt; 5 h, reflux; reflux → rt
1.2 Catalysts: Piperidine ;  15 h, rt
Reference
One-pot preparation of caffeic acid esters from 3,4-dihydroxybenzaldehyde
Hu, Wei-Xiao; et al, Journal of Chemical Research, 2006, (9), 586-588

Production Method 2

Reaction Conditions
1.1 Reagents: Sulfuric acid Solvents: Isopropanol ;  3 - 6 min, reflux
Reference
Design and synthesis of novel aspirin-caffeic acid ester hybrids for cardioprotection with reduced risk of hemorrhagic stroke
Shi, Zhi-Hao; et al, Asian Journal of Chemistry, 2015, 27(4), 1342-1346

Production Method 3

Reaction Conditions
1.1 Reagents: Thionyl chloride Solvents: 1,4-Dioxane ;  rt; 1 h, reflux
1.2 1 h, reflux; 17 - 24 h, reflux
Reference
Inhibitory effect of the alkyl side chain of caffeic acid analogues on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages
Uwai, Koji; et al, Bioorganic & Medicinal Chemistry, 2008, 16(16), 7795-7803

Production Method 4

Reaction Conditions
1.1 Reagents: Triphenylphosphine ,  Iodine Solvents: Acetonitrile ;  10 min, rt
1.2 Catalysts: Zinc triflate ;  30 min, 60 °C
1.3 Solvents: Acetonitrile ;  5 h, 60 °C
Reference
Zn(OTf)2-Promoted Chemoselective Esterification of Hydroxyl Group Bearing Carboxylic Acids
Mamidi, Narsimha; et al, Journal of Organic Chemistry, 2013, 78(6), 2386-2396

Production Method 5

Reaction Conditions
1.1 Solvents: Toluene ;  5 h, reflux; reflux → rt
1.2 Reagents: Pyridine ,  Piperidine ;  8 - 24 h, rt
Reference
Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines
Xia, Chun-nian; et al, Bioorganic & Medicinal Chemistry Letters, 2008, 18(24), 6553-6557

Production Method 6

Reaction Conditions
Reference
Antioxidant phenolic esters with potential anticancer activity: a Raman spectroscopy study
Calheiros, R.; et al, Journal of Raman Spectroscopy, 2008, 39(1), 95-107

Production Method 7

Reaction Conditions
1.1 Catalysts: Sulfuric acid Solvents: Isopropanol ;  2 h, reflux
Reference
Antiproliferative, antiandrogenic and cytotoxic effects of novel caffeic acid derivatives in LNCaP human androgen-dependent prostate cancer cells
Sanderson, J. Thomas; et al, Bioorganic & Medicinal Chemistry, 2013, 21(22), 7182-7193

Production Method 8

Reaction Conditions
1.1 heated
Reference
Biological activity evaluation and structure-activity relationships analysis of ferulic acid and caffeic acid derivatives for anticancer
Li, Weixia; et al, Bioorganic & Medicinal Chemistry Letters, 2012, 22(19), 6085-6088

2-Propenoic acid,3-(3,4-dihydroxyphenyl)-, 1-methylethyl ester, (2E)- Raw materials

2-Propenoic acid,3-(3,4-dihydroxyphenyl)-, 1-methylethyl ester, (2E)- Preparation Products

2-Propenoic acid,3-(3,4-dihydroxyphenyl)-, 1-methylethyl ester, (2E)- Related Literature

Related Categories

845883-03-6 (2-Propenoic acid,3-(3,4-dihydroxyphenyl)-, 1-methylethyl ester, (2E)-) Related Products

Recommended suppliers
Shandong Jing Kun Chemical Co.,Ltd.
Gold Member
Audited Supplier Audited Supplier
CN Supplier
Bulk
Shandong Jing Kun Chemical Co.,Ltd.
Zhangzhou Sinobioway Peptide Co.,Ltd.
Gold Member
Audited Supplier Audited Supplier
CN Supplier
Reagent
Zhangzhou Sinobioway Peptide Co.,Ltd.
上海嶸奧生物技術(shù)有限公司
Gold Member
Audited Supplier Audited Supplier
CN Supplier
Reagent
上海嶸奧生物技術(shù)有限公司
Inner Mongolia Xinhong Biological Technology Co., Ltd
Gold Member
Audited Supplier Audited Supplier
CN Supplier
Bulk
Inner Mongolia Xinhong Biological Technology Co., Ltd
TAIXING JOXIN BIO-TEC CO.,LTD.
Gold Member
Audited Supplier Audited Supplier
CN Supplier
Bulk
TAIXING JOXIN BIO-TEC CO.,LTD.