CAS 480-40-0|chrysin|Chrysin|5,7-Dihydroxyflavone|5,7-dihydroxy-2-phenyl-4H-chromen-4-one|CHRYSINE|5,7-二羟黄酮|Chrysin|柯因|5,7-Dihydroxy-2-phenyl-4H-1-benzopyran-4-one|NSC 407436|Crysin|5,7-Dihydr...

General Information

Structure

Molecular Formula

C₁₅H₁₀O₄

Molecular Mass

254.2375

Exact Mass

254.0579088

Charge

InChI

InChI=1S/C15H10O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-8,16-17H

InChIKey

RTIXKCRFFJGDFG-UHFFFAOYSA-N

Canonic Smiles

Oc1cc(O)c2c(c1)oc(cc2=O)c1ccccc1

Isomeric Smiles

c12c(=O)cc(oc1cc(cc2O)O)c1ccccc1

Calculated Properties

JChem

Acid pKa

6.577777

H Acceptors

H Donor

LogD (pH = 5.5)

2.9755785

LogD (pH = 7.4)

2.0891845

Log P

3.0102544

Molar Refractivity

70.933

Polarizability

26.480106

Polar Surface Area

66.76

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC Traditional name

chrysin 5,7-dihydroxy-2-phenyl-4H-chromen-4-one

IUPAC name

5,7-dihydroxy-2-phenyl-4H-chromen-4-one

Synonyms

Chrysin5,7-DihydroxyflavoneCHRYSINE5,7-二羟黄酮柯因Chrysin5,7-Dihydroxy-2-phenyl-4H-1-benzopyran-4-one5,7-Dihydroxy-2-phenylchromen-4-oneCrysinNSC 407436Chrysinic acidChrysin5,7-二羟基黄酮5,7-DihydroxyflavoneNP-005901Galangin flavanone5,7-Dihydroxy-2-phenyl-4H-chromen-4-one

Names and Identifiers

Registration numbers

CAS Number

480-40-0

EC Number

207-549-7

PubChem SID

2485645516206450924893009

Beilstein Number

Merck Index

MDL Number

PubChem CID

CHEMBL

Chemspider ID

KEGG ID

Unique Ingredient Identifier

3CN01F5ZJ5

Wikipedia Title

Chrysin

Registration numbers

Properties

Pharmacology Properties

Gene Information

human ... CDC2(983), CDK5(1020), CDK6(1021), CYP19A1(1588), CYP1A2(1544), GSK3A(2931)mouse ... Hexa(15211), Ptgs2(19225)rat ... Gabra2(29706)

Mechanism of Action

Lipid peroxidation inhibitor in rat liver microsomes

Physical Property

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Selleck Chemicals

S2281

Research Area: Inflammation
Biological Activity:
Chrysin is a naturally occurring flavone chemically extracted from the blue passion flower (Passiflora caerulea). [1] It has been shown to induce an anti-inflammatory effect, most likely by inhibition of COX-2 expression and via IL-6 signaling.[2] In rodent in vivo studies, chrysin was found anxiolytic. However asbestos was not known to cause cancer because it did not cause cancer in non-human animals

MP Biomedicals

02154985

(5,7-Dihydroxyflavone) Crystalline

05210927

MP Biomedicals Rare Chemical collection

Wikipedia

Chrysin

Sigma Aldrich

C80105

Packaging
25 g in glass bottle

TRC

C432730

Chrysin is a flavanoid with anti-inflammatory effect and potential protective effects against cancer and cardiovascular disease. Studies show that Chrysin is central benzodiazepine receptor ligand with possible anxiolytic effects. Chrysin was initially be

Molecule Details

References

PubChem Literature

From Data Sources

• Woo KJ et al. FEBS Lett. 2005 Jan 31;579(3):705-11.

• O’Leary, K.A. et al.: Mutat. Res., 551, 245 (2004)

• Saarinen, N. et al.: J. Steroid Biochem. Mol. Biol., 78, 231 (2004)

• Wolfman, C. et al.: Pharmacol. Biochem. Behav., 47, 1 (2004)

• Katyal, M. et al., Talanta, 1968, 15, 95, (detn, U)

• Batterham, T.J. et al., Aust. J. Chem., 1964, 17, 428, (pmr)

• Marsh, C.A., Biochem. J., 1955, 59, 58, (isol, deriv)

• Nevskaya, E.M. et al., Zh. Anal. Khim., 1972, 27, 1699, (reactions)

• Wagner, H. et al., Tet. Lett., 1976, 1799, (cmr)

• Rashad, M.A. et al., Phytomedicine, 1998, 5, 375-381, (isol, activity)

• Kingston, D.G.I. et al., Tetrahedron, 1973, 29, 4083, (ms)

• Bowie, J.H. et al., J.C.S.(B), 1969, 89, (ms)

• Wollenweber, E. et al., Planta Med., 1985, 50, 459, (isol)

• Nadkarni, D.R. et al., J.C.S., 1938, 1320, (synth)

• Katyal, M. et al., Proc. - Indian Acad. Sci., Sect. A, 1962, 56, 125; CA, 58, 3884c, (detn, Th)

• Jung, J.H. et al., Phytochemistry, 1990, 29, 1271, (pmr, cmr)

• Litkei, G. et al., Annalen, 1995, 1711, (synth, pmr)

• Hounghton, P.J. et al., Pharm. Pharmacol. Lett., 1997, 7, 96-98, (activity)

• Gaydon, E.M. et al., Bull. Soc. Chim. Fr., Part II, 1978, 43, (synth, uv, cmr)

• Saxena, S. et al., Synthesis, 1985, 697, (synth)

• Jaipetch, T. et al., Phytochemistry, 1983, 22, 625, (isol)

• Asakawa, Y., Bull. Chem. Soc. Jpn., 1971, 44, 2761, (isol)

• Davoust, D. et al., Org. Magn. Reson., 1978, 11, 547, (pmr)

• Le Floc'h, Y. et al., Tet. Lett., 1986, 27, 5503, (synth)

• Dev, B. et al., Fresenius' Z. Anal. Chem., 1963, 196, 178, (synth, use, deriv)

• Agrawal, P.K. et al., Tet. Lett., 1983, 177, (cmr)

• Lee, J.-M. et al., Synthesis, 2001, 2247-2254, (synth, pmr, cmr)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 95C, (ir)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 918C, (nmr)

• The Flavonoids: Advances in Research since 1980, (Ed. Harborne, J.B.), Chapman and Hall, London, 1988

• Shen, C.-C. et al., Phytochemistry, 1993, 34, 843, (pmr, cmr)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

chrysin 5,7-dihydroxy-2-phenyl-4H-chromen-4-one

IUPAC name

5,7-dihydroxy-2-phenyl-4H-chromen-4-one

Synonyms

Registration numbers

CAS Number

480-40-0

EC Number

207-549-7

PubChem SID

2485645516206450924893009

Beilstein Number

Merck Index

MDL Number

PubChem CID

CHEMBL

Chemspider ID

KEGG ID

Unique Ingredient Identifier

Wikipedia Title

Molecule Details

S2281

(5,7-Dihydroxyflavone) Crystalline

05210927

MP Biomedicals Rare Chemical collection

Wikipedia

Chrysin

Sigma Aldrich

C80105

Packaging
25 g in glass bottle

TRC

C432730

References

PubChem Literature

From Data Sources

• Woo KJ et al. FEBS Lett. 2005 Jan 31;579(3):705-11.

• O’Leary, K.A. et al.: Mutat. Res., 551, 245 (2004)

• Saarinen, N. et al.: J. Steroid Biochem. Mol. Biol., 78, 231 (2004)

• Wolfman, C. et al.: Pharmacol. Biochem. Behav., 47, 1 (2004)

• Katyal, M. et al., Talanta, 1968, 15, 95, (detn, U)

• Batterham, T.J. et al., Aust. J. Chem., 1964, 17, 428, (pmr)

• Marsh, C.A., Biochem. J., 1955, 59, 58, (isol, deriv)

• Nevskaya, E.M. et al., Zh. Anal. Khim., 1972, 27, 1699, (reactions)

• Wagner, H. et al., Tet. Lett., 1976, 1799, (cmr)

• Rashad, M.A. et al., Phytomedicine, 1998, 5, 375-381, (isol, activity)

• Kingston, D.G.I. et al., Tetrahedron, 1973, 29, 4083, (ms)

• Bowie, J.H. et al., J.C.S.(B), 1969, 89, (ms)

• Wollenweber, E. et al., Planta Med., 1985, 50, 459, (isol)

• Nadkarni, D.R. et al., J.C.S., 1938, 1320, (synth)

• Katyal, M. et al., Proc. - Indian Acad. Sci., Sect. A, 1962, 56, 125; CA, 58, 3884c, (detn, Th)

• Jung, J.H. et al., Phytochemistry, 1990, 29, 1271, (pmr, cmr)

• Litkei, G. et al., Annalen, 1995, 1711, (synth, pmr)

• Hounghton, P.J. et al., Pharm. Pharmacol. Lett., 1997, 7, 96-98, (activity)

• Gaydon, E.M. et al., Bull. Soc. Chim. Fr., Part II, 1978, 43, (synth, uv, cmr)

• Saxena, S. et al., Synthesis, 1985, 697, (synth)

• Jaipetch, T. et al., Phytochemistry, 1983, 22, 625, (isol)

• Asakawa, Y., Bull. Chem. Soc. Jpn., 1971, 44, 2761, (isol)

• Davoust, D. et al., Org. Magn. Reson., 1978, 11, 547, (pmr)

• Le Floc'h, Y. et al., Tet. Lett., 1986, 27, 5503, (synth)

• Dev, B. et al., Fresenius' Z. Anal. Chem., 1963, 196, 178, (synth, use, deriv)

• Agrawal, P.K. et al., Tet. Lett., 1983, 177, (cmr)

• Lee, J.-M. et al., Synthesis, 2001, 2247-2254, (synth, pmr, cmr)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 95C, (ir)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 918C, (nmr)

• The Flavonoids: Advances in Research since 1980, (Ed. Harborne, J.B.), Chapman and Hall, London, 1988

• Shen, C.-C. et al., Phytochemistry, 1993, 34, 843, (pmr, cmr)

Bioactivity

PubChem BioAssay

Properties

Pharmacology Properties

Gene Information

human ... CDC2(983), CDK5(1020), CDK6(1021), CYP19A1(1588), CYP1A2(1544), GSK3A(2931)mouse ... Hexa(15211), Ptgs2(19225)rat ... Gabra2(29706)

Mechanism of Action

Lipid peroxidation inhibitor in rat liver microsomes

Physical Property

Molecule

ID:59746