CAS 537-73-5|CAS 25522-33-2|isoferulic acid|(2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid|(2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid|3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid|3-(...

General Information

Structure

Molecular Formula

C₁₀H₁₀O₄

Molecular Mass

194.184

Exact Mass

194.0579088

Charge

InChI

InChI=1S/C10H10O4/c1-14-9-4-2-7(6-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+

InChIKey

QURCVMIEKCOAJU-HWKANZROSA-N

Canonic Smiles

COc1ccc(cc1O)/C=C/C(=O)O

Isomeric Smiles

COc1ccc(cc1O)/C=C/C(=O)O

Calculated Properties

JChem

LogD (pH = 7.4)

-1.64

LogD (pH = 5.5)

-0.15

Log P

1.67

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

3.68

Polar Surface Area

66.76

Polarizability

19.36

Molar Refractivity

51.50

LOG S

-1.72

Data Source

Names and Identifiers

IUPAC Traditional name

isoferulic acid 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid (2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid

IUPAC name

(2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid

Synonyms

(2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid3-HYDROXY-4-METHOXYCINNAMIC ACID3-Hydroxy-4-methoxycinnamic acid, predominantly trans3-羟基-4-甲氧基肉桂酸，主要为反式3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic Acid3-(3-Hydroxy-4-methoxyphenyl)acrylic Acid3-Hydroxy-4-methoxycinnamic Acid (Isoferulic Acid)Isoferulic Acid3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acidHesperetic acidHesperetinic acidIsoferulic acid3-羟基-4-甲氧基肉桂酸, 主体成分为反式trans-Isoferulic acidtrans-3-Hydroxy-4-methoxycinnamic acidtrans-3-(3-Hydroxy-4-methoxyphenyl)acrylic acid3-Hydroxy-4-methoxycinnamic acidHesperetic acidisoferulic acid

Names and Identifiers

Registration numbers

PubChem SID

2484659116096819499443580160644657

MDL Number

CAS Number

EC Number

PubChem CID

Beilstein Number

Reaxys Registry

BKMS React Database

KEGG ID

PubMed Citation Links

18314290227702252194189921937734

BRENDA Database

2.4.1.1772.7.4.22.4.1.351.14.18.13.1.1.493.1.1.732.1.1.3361.17.3.23.2.1.202.4.1.1216.2.1.12

BRENDA Ligand Database

15798196474598132799

MetaboLights Database

MTBLS2542MTBLS3657MTBLS312MTBLS309MTBLS2096MTBLS3935MTBLS1906MTBLS2406MTBLS526MTBLS1801MTBLS1903MTBLS4463MTBLS20

HMDB Database

CHEMBL

Protein Data Bank

Patent number

ACToR Database

CHEBI ID

CHEBI:27794CHEBI:24888CHEBI:6010

SABIO-RK Database

KNApSAcK Database

PDBeChem Database

BindingDB Database

DrugBank ID

SureChEMBL Database

Registration numbers

Properties

Pharmacology Properties

Mechanism of Action

Lowers plasma glucose levels

Properties

Related Proteins

PDB Bank

3CBG

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

MP Biomedicals

05210655

MP Biomedicals Rare Chemical collection

Sigma Aldrich

103012

Packaging
1, 5 g in glass bottle

TRC

H946180

3-Hydroxy-4-methoxycinnamic Acid (Isoferulic acid) is a hypoglycemic agent.

DrugBank

DB07109

Drug information: experimental

ChEBI

CHEBI:27794

A ferulic acid consisting of trans-cinnamic acid bearing methoxy and hydroxy substituents at positions 4 and 3 respectively on the phenyl ring.

Molecule Details

References

PubChem Literature

From Data Sources

• Liu, I.-M., et al.: J. Pharmacol. Exp. Ther., 307, 1196 (2003)

• Bowden, B.F. et al., Aust. J. Chem., 1975, 28, 91, (derivs)

• Kelley, C.J. et al., J.O.C., 1976, 41, 449, (cmr)

• Desai, M.N. et al., CA, 1973, 79, 111369c, (detn, Fe)

• de Silva, S.O. et al., Can. J. Chem., 1979, 57, 1598, (synth, deriv)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1057C; 1058B, (nmr)

• Blase, F.R. et al., Synth. Commun., 1995, 25, 3187, (synth, Isoferulic acid)

• Achenbach, H. et al., Chem. Ber., 1971, 104, 1468, (isol, deriv)

• Bate-Smith, E.C., Sci. Proc. R. Dublin Soc., 1956, 27, 165, (occur)

• Stuart, J.G. et al., J. Het. Chem., 1987, 24, 1589, (synth, ir, pmr, deriv)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 184B; 184D, (ir)

• Dewick, P.M. et al., Chem. Comm., 1968, 673, (biosynth)

• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, no. 957

• Garcia-Granda, S. et al., Acta Cryst. C, 1987, 43, 683, (cryst struct)

• Souleman, A.A.M. et al., Nat. Prod. Sci., 1998, 4, 245-252, (Isoferulic acid 3'-sulfate)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CAK375

• Hermann, F.X., Pharmazie, 1956, 11, 433, (rev)

• Swain, T. et al., Phytochemistry, 1970, 9, 2115, (biosynth)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

isoferulic acid 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid (2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid

IUPAC name

(2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid

Synonyms

Registration numbers

PubChem SID

2484659116096819499443580160644657

MDL Number

CAS Number

EC Number

PubChem CID

Beilstein Number

Reaxys Registry

BKMS React Database

KEGG ID

PubMed Citation Links

18314290227702252194189921937734

BRENDA Database

2.4.1.1772.7.4.22.4.1.351.14.18.13.1.1.493.1.1.732.1.1.3361.17.3.23.2.1.202.4.1.1216.2.1.12

BRENDA Ligand Database

15798196474598132799

MetaboLights Database

MTBLS2542MTBLS3657MTBLS312MTBLS309MTBLS2096MTBLS3935MTBLS1906MTBLS2406MTBLS526MTBLS1801MTBLS1903MTBLS4463MTBLS20

HMDB Database

CHEMBL

Protein Data Bank

Patent number

ACToR Database

CHEBI ID

CHEBI:27794CHEBI:24888CHEBI:6010

SABIO-RK Database

KNApSAcK Database

PDBeChem Database

BindingDB Database

DrugBank ID

SureChEMBL Database

Related Proteins

Molecule Details

MP Biomedicals Rare Chemical collection

Sigma Aldrich

103012

Packaging
1, 5 g in glass bottle

TRC

H946180

3-Hydroxy-4-methoxycinnamic Acid (Isoferulic acid) is a hypoglycemic agent.

DrugBank

DB07109

Drug information: experimental

ChEBI

CHEBI:27794

A ferulic acid consisting of trans-cinnamic acid bearing methoxy and hydroxy substituents at positions 4 and 3 respectively on the phenyl ring.

References

PubChem Literature

From Data Sources

• Liu, I.-M., et al.: J. Pharmacol. Exp. Ther., 307, 1196 (2003)

• Bowden, B.F. et al., Aust. J. Chem., 1975, 28, 91, (derivs)

• Kelley, C.J. et al., J.O.C., 1976, 41, 449, (cmr)

• Desai, M.N. et al., CA, 1973, 79, 111369c, (detn, Fe)

• de Silva, S.O. et al., Can. J. Chem., 1979, 57, 1598, (synth, deriv)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1057C; 1058B, (nmr)

• Blase, F.R. et al., Synth. Commun., 1995, 25, 3187, (synth, Isoferulic acid)

• Achenbach, H. et al., Chem. Ber., 1971, 104, 1468, (isol, deriv)

• Bate-Smith, E.C., Sci. Proc. R. Dublin Soc., 1956, 27, 165, (occur)

• Stuart, J.G. et al., J. Het. Chem., 1987, 24, 1589, (synth, ir, pmr, deriv)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 184B; 184D, (ir)

• Dewick, P.M. et al., Chem. Comm., 1968, 673, (biosynth)

• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, no. 957

• Garcia-Granda, S. et al., Acta Cryst. C, 1987, 43, 683, (cryst struct)

• Souleman, A.A.M. et al., Nat. Prod. Sci., 1998, 4, 245-252, (Isoferulic acid 3'-sulfate)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CAK375

• Hermann, F.X., Pharmazie, 1956, 11, 433, (rev)

• Swain, T. et al., Phytochemistry, 1970, 9, 2115, (biosynth)

Bioactivity

PubChem BioAssay

Properties

Pharmacology Properties

Mechanism of Action

Lowers plasma glucose levels

Molecule

ID:4762