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Product No: CH1653

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one, 95%

Name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
Brand: Chempure
Rating: 4 (1 reviews)

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CAS Number

520-36-5

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IUPAC name	5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
inchi	InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H
inchi key	KZNIFHPLKGYRTM-UHFFFAOYSA-N
molecular formula	C15H10O5
synonyms	apigenin 520-36-5 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one Versulin Apigenol
Compound Description	Apigenin is a trihydroxyflavone that is flavone substituted by hydroxy groups at positions 4', 5 and 7. It induces autophagy in leukaemia cells. It has a role as a metabolite and an antineoplastic agent. It is a conjugate acid of an apigenin-7-olate. Apigenin has been reported in Camellia sinensis, Apis, and other organisms with data available. Apigenin is a plant-derived flavonoid that has significant promise as a skin cancer chemopreventive agent. Apigenin inhibits the expression of involucrin , a marker of keratinocyte differentiation, is increased by differentiating agents via a protein kinase Cdelta , Ras, MEKK1, MEK3 cascade that increases AP1 factor level and AP1 factor binding to DNA elements in the hINV promoter. Apigenin suppresses the 12-O-tetradeconylphorbol-13-acetate-dependent increase in AP1 factor expression and binding to the hINV promoter and the increase in hINV promoter activity. Apigenin also inhibits the increase in promoter activity observed following overexpression of PKCdelta, constitutively active Ras, or MEKK1. The suppression of PKCdelta activity is associated with reduced phosphorylation of PKCdelta-Y311. Activation of hINV promoter activity by the green tea polyphenol, -epigellocathecin-3-gallate, is also inhibited by apigenin, suggesting that the two chemopreventive agents can produce opposing actions in keratinocytes. . Apigenin, a flavone abundantly found in fruits and vegetables, exhibits antiproliferative, anti-inflammatory, and antimetastatic activities through poorly defined mechanisms. This flavonoid provides selective activity to promote caspase-dependent-apoptosis of leukemia cells and uncover an essential role of PKCdelta during the induction of apoptosis by apigenin. . Apigenin markedly induces the expression of death receptor 5 and synergistically acts with exogenous soluble recombinant human tumor necrosis factor-related apoptosis-inducing ligand to induce apoptosis in malignant tumor cells. On the other hand, apigenin-mediated induction of DR5 expression is not observed in normal human peripheral blood mononuclear cells. Moreover, apigenin does not sensitize normal human peripheral blood mononuclear cells to TRAIL-induced apoptosis. . 5,7,4'-trihydroxy-flavone, one of the FLAVONES. See also: Flavone ; Chamomile ; Fenugreek seed ... View More ...

Computed Properties

Molecular Weight:	270.24 g/mol
XLogP3:	1.7
Hydrogen Bond Donor Count:	3
Hydrogen Bond Acceptor Count:	5
Rotatable Bond Count:	1
Exact Mass:	270.05282342 g/mol
Monoisotopic Mass:	270.05282342 g/mol
Topological Polar Surface Area:	87 Å²
Heavy Atom Count:	20
Formal Charge:	0
Complexity:	411
Isotope Atom Count:	0
Defined Atom Stereocenter Count:	0
Undefined Atom Stereocenter Count:	0
Defined Bond Stereocenter Count:	0
Undefined Bond Stereocenter Count:	0
Covalently-Bonded Unit Count:	1
Compound Is Canonicalized:	Yes

hazard signal	Warning
hazard classes and categories	Skin Irrit. 2 (75.5%) Eye Irrit. 2 (75.5%) STOT SE 3 (74.5%) Skin Irrit. 2 (28.3%) Aquatic Chronic 3 (71.7%)
precautionary statement codes	P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501
hazard statements	H315 (75.5%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (75.5%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H335 (74.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

symptoms
carcinogen classification	default_key: No indication of carcinogenicity to humans .

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*This document is like a lab demo—an example Certificate of Analysis (COA) that showcases what a COA looks like but may not match the latest batch in all its glory. Think of it as a chemistry experiment: close, but not quite the final reaction!

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About this item

IUPAC name	5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
inchi	InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H
inchi key	KZNIFHPLKGYRTM-UHFFFAOYSA-N
molecular formula	C15H10O5
synonyms	apigenin 520-36-5 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one Versulin Apigenol
Compound Description	Apigenin is a trihydroxyflavone that is flavone substituted by hydroxy groups at positions 4', 5 and 7. It induces autophagy in leukaemia cells. It has a role as a metabolite and an antineoplastic agent. It is a conjugate acid of an apigenin-7-olate. Apigenin has been reported in Camellia sinensis, Apis, and other organisms with data available. Apigenin is a plant-derived flavonoid that has significant promise as a skin cancer chemopreventive agent. Apigenin inhibits the expression of involucrin , a marker of keratinocyte differentiation, is increased by differentiating agents via a protein kinase Cdelta , Ras, MEKK1, MEK3 cascade that increases AP1 factor level and AP1 factor binding to DNA elements in the hINV promoter. Apigenin suppresses the 12-O-tetradeconylphorbol-13-acetate-dependent increase in AP1 factor expression and binding to the hINV promoter and the increase in hINV promoter activity. Apigenin also inhibits the increase in promoter activity observed following overexpression of PKCdelta, constitutively active Ras, or MEKK1. The suppression of PKCdelta activity is associated with reduced phosphorylation of PKCdelta-Y311. Activation of hINV promoter activity by the green tea polyphenol, -epigellocathecin-3-gallate, is also inhibited by apigenin, suggesting that the two chemopreventive agents can produce opposing actions in keratinocytes. . Apigenin, a flavone abundantly found in fruits and vegetables, exhibits antiproliferative, anti-inflammatory, and antimetastatic activities through poorly defined mechanisms. This flavonoid provides selective activity to promote caspase-dependent-apoptosis of leukemia cells and uncover an essential role of PKCdelta during the induction of apoptosis by apigenin. . Apigenin markedly induces the expression of death receptor 5 and synergistically acts with exogenous soluble recombinant human tumor necrosis factor-related apoptosis-inducing ligand to induce apoptosis in malignant tumor cells. On the other hand, apigenin-mediated induction of DR5 expression is not observed in normal human peripheral blood mononuclear cells. Moreover, apigenin does not sensitize normal human peripheral blood mononuclear cells to TRAIL-induced apoptosis. . 5,7,4'-trihydroxy-flavone, one of the FLAVONES. See also: Flavone ; Chamomile ; Fenugreek seed ... View More ...

Computed Properties

Molecular Weight:	270.24 g/mol
XLogP3:	1.7
Hydrogen Bond Donor Count:	3
Hydrogen Bond Acceptor Count:	5
Rotatable Bond Count:	1
Exact Mass:	270.05282342 g/mol
Monoisotopic Mass:	270.05282342 g/mol
Topological Polar Surface Area:	87 Å²
Heavy Atom Count:	20
Formal Charge:	0
Complexity:	411
Isotope Atom Count:	0
Defined Atom Stereocenter Count:	0
Undefined Atom Stereocenter Count:	0
Defined Bond Stereocenter Count:	0
Undefined Bond Stereocenter Count:	0
Covalently-Bonded Unit Count:	1
Compound Is Canonicalized:	Yes

hazard signal	Warning
hazard classes and categories	Skin Irrit. 2 (75.5%) Eye Irrit. 2 (75.5%) STOT SE 3 (74.5%) Skin Irrit. 2 (28.3%) Aquatic Chronic 3 (71.7%)
precautionary statement codes	P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501
hazard statements	H315 (75.5%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (75.5%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H335 (74.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

symptoms
carcinogen classification	default_key: No indication of carcinogenicity to humans .

Product No: CH1653

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one, 95%

Product No: CH1653

About this item

NAME AND IDENTIFIERS

CHEMICAL AND PHYSICAL PROPERTIES

SAFETY AND HAZARDS

TOXICITY

About this item

Documentation

Certificate of Analysis

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Reviews

Product No: CH1653

About this item

NAME AND IDENTIFIERS

CHEMICAL AND PHYSICAL PROPERTIES

SAFETY AND HAZARDS

TOXICITY

Require a Sample Certificate of Analysis (COA) ?