2-Benzal-4-hydroxyacetophenone

Modify Date: 2025-08-21 16:47:12

2-Benzal-4-hydroxyacetophenone Structure
2-Benzal-4-hydroxyacetophenone structure
 Common Name 2-Benzal-4-hydroxyacetophenone
CAS Number 2657-25-2 Molecular Weight 224.25500
Density 1.191 g/cm3 Boiling Point 419.6ºC at 760 mmHg
Molecular Formula C15H12O2 Melting Point 174-178 °C
MSDS USA Flash Point 179.1ºC

 Use of 2-Benzal-4-hydroxyacetophenone


4'-Hydroxychalcone, a chalcone isolated from licorice root, with hepatoprotective activity. 4'-Hydroxychalcone inhibits TNFα-induced NF-κB activation via proteasome inhibition. 4'-Hydroxychalcone induces a rapid potassium release from mitochondrial vesicles and causes deterioration of respiratory control and oxidative phosphorylation of isolated rat liver mitochondria[1][2][3].

 Names

Name 4'-hydroxychalcone
Synonym More Synonyms

 2-Benzal-4-hydroxyacetophenone Biological Activity

Description 4'-Hydroxychalcone, a chalcone isolated from licorice root, with hepatoprotective activity. 4'-Hydroxychalcone inhibits TNFα-induced NF-κB activation via proteasome inhibition. 4'-Hydroxychalcone induces a rapid potassium release from mitochondrial vesicles and causes deterioration of respiratory control and oxidative phosphorylation of isolated rat liver mitochondria[1][2][3].
Related Catalog
References

[1]. Inoue B, et al. The effects of echinatin and its related compounds on the mitochondrial energy transfer reaction. J Toxicol Sci. 1982 Nov;7(4):245-54.

[2]. Ali Reza, et al. Hepatoprotective activity of phloretin and hydroxychalcones against Acetaminophen Induced hepatotoxicity in mice. Iranian Journal of Pharmaceutical Sciences. 2011 Jan; 7(2).

[3]. Orlikova B, et al. The aromatic ketone 4'-hydroxychalcone inhibits TNFα-induced NF-κB activation via proteasome inhibition. Biochem Pharmacol. 2011 Sep 15;82(6):620-31.

 Chemical & Physical Properties

Density 1.191 g/cm3
Boiling Point 419.6ºC at 760 mmHg
Melting Point 174-178 °C
Molecular Formula C15H12O2
Molecular Weight 224.25500
Flash Point 179.1ºC
Exact Mass 224.08400
PSA 37.30000
LogP 3.28830
Vapour Pressure 1.23E-07mmHg at 25°C
Index of Refraction 1.653
InChIKey UAHGNXFYLAJDIN-IZZDOVSWSA-N
SMILES O=C(C=Cc1ccccc1)c1ccc(O)cc1

 Safety Information

Hazard Codes Xi: Irritant;
Risk Phrases R36/37/38
Safety Phrases S37/39-S26

 Synthetic Route

Benzaldehyde structure

Benzaldehyde

CAS#:100-52-7

4-Hydroxyacetophenone structure

4-Hydroxyacetop...

CAS#:99-93-4

~98%

2-Benzal-4-hydroxyacetophenone Structure

2-Benzal-4-hydr...

CAS#:2657-25-2

Literature: Rafiee, Ezzat; Rahimi, Farzaneh Monatshefte fur Chemie, 2013 , vol. 144, # 3 p. 361 - 367
4'-Methoxychalcone structure

4'-Methoxychalcone

CAS#:22966-19-4

~99%

2-Benzal-4-hydroxyacetophenone Structure

2-Benzal-4-hydr...

CAS#:2657-25-2

Literature: Gavande, Navnath S.; Kundu, Sonia; Badgujar, Naresh S.; Kaur, Gurmeet; Chakraborti, Asit K. Tetrahedron, 2006 , vol. 62, # 17 p. 4201 - 4204
4-Hydroxyacetophenone structure

4-Hydroxyacetop...

CAS#:99-93-4

~%

2-Benzal-4-hydroxyacetophenone Structure

2-Benzal-4-hydr...

CAS#:2657-25-2

Literature: Manna, Fedele; Chimenti, Franco; Fioravanti, Rossella; Bolasco, Adriana; Secci, Daniela; Chimenti, Paola; Ferlini, Cristiano; Scambia, Giovanni Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 20 p. 4632 - 4635
N/A structure

N/A

CAS#:468060-22-2

~16%

2-Benzal-4-hydroxyacetophenone Structure

2-Benzal-4-hydr...

CAS#:2657-25-2

Literature: Liu; Wilairat; Go Journal of Medicinal Chemistry, 2001 , vol. 44, # 25 p. 4443 - 4452
1-[4-(Tetrahydro-pyran-2-yloxy)-phenyl]-ethanone structure

1-[4-(Tetrahydr...

CAS#:16162-69-9

Benzaldehyde structure

Benzaldehyde

CAS#:100-52-7

~84%

2-Benzal-4-hydroxyacetophenone Structure

2-Benzal-4-hydr...

CAS#:2657-25-2

Literature: Lin, Chun-Nan; Lee, Tai-Hua; Hsu, Mei-Feng; Wang, Jih-Pyang; Ko, Feng-Nien; Teng, Che-Ming Journal of Pharmacy and Pharmacology, 1997 , vol. 49, # 5 p. 530 - 536
1-[4-(Tetrahydro-pyran-2-yloxy)-phenyl]-ethanone structure

1-[4-(Tetrahydr...

CAS#:16162-69-9

~%

2-Benzal-4-hydroxyacetophenone Structure

2-Benzal-4-hydr...

CAS#:2657-25-2

Literature: Sogawa; Nihro; Ueda; Izumi; Miki; Matsumoto; Satoh Journal of Medicinal Chemistry, 1993 , vol. 36, # 24 p. 3904 - 3909
Cinnamic acid structure

Cinnamic acid

CAS#:140-10-3

Phenol structure

Phenol

CAS#:108-95-2

~%

2-Benzal-4-hydroxyacetophenone Structure

2-Benzal-4-hydr...

CAS#:2657-25-2

Literature: Nakazawa et al. Yakugaku Zasshi, 1954 , vol. 74, p. 495 Chem.Abstr., 1955 , p. 8182
phenyl (E)-3-phenylprop-2-enoate structure

phenyl (E)-3-ph...

CAS#:2757-04-2

~%

2-Propen-1-one,1-(2-hydroxyphenyl)-3-phenyl-, (2E)- structure

2-Propen-1-one,...

CAS#:888-12-0

2-Benzal-4-hydroxyacetophenone Structure

2-Benzal-4-hydr...

CAS#:2657-25-2

Literature: Singh, A.K.; Raghuraman, T.S. Tetrahedron Letters, 1985 , vol. 26, # 34 p. 4125 - 4128

 Synonyms

MFCD00016484
2-BENZAL-4'-HYDROXYACETOPHENONE
BENZYLIDENE-4'-HYDROXYACETOPHENONE
4'-HYDROXYCHALCONE
HYDROXYCHALCONE,4'
4′-Hydroxychalcone
1-(4-Hydroxyphenyl)-3-phenylprop-2-en-1-one
2-Benzylidene-4'-hydroxyacetophenone
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