2',4,4',6'-TETRAHYDROXYCHALCONE

Modify Date: 2025-08-24 13:26:56

2',4,4',6'-TETRAHYDROXYCHALCONE Structure
2',4,4',6'-TETRAHYDROXYCHALCONE structure
Common Name 2',4,4',6'-TETRAHYDROXYCHALCONE
CAS Number 25515-46-2 Molecular Weight 272.25300
Density 1.483±0.06 g/cm3(Predicted) Boiling Point 538.7±50.0 °C(Predicted)
Molecular Formula C15H12O5 Melting Point N/A
MSDS N/A Flash Point N/A

 Use of 2',4,4',6'-TETRAHYDROXYCHALCONE


(E)-Naringenin chalcone is an orally active anti-allergic agent. (E)-Naringenin chalcone also has antioxidant, anti-inflammatory activities. (E)-Naringenin chalcone can improve adipocyte functions. (E)-Naringenin chalcone inhibits histamine release from rat peritoneal mast cell[1][2][4].

 Names

Name Naringenin chalcone,2',4,4',6'-Tetrahydroxychalcone
Synonym More Synonyms

 2',4,4',6'-TETRAHYDROXYCHALCONE Biological Activity

Description (E)-Naringenin chalcone is an orally active anti-allergic agent. (E)-Naringenin chalcone also has antioxidant, anti-inflammatory activities. (E)-Naringenin chalcone can improve adipocyte functions. (E)-Naringenin chalcone inhibits histamine release from rat peritoneal mast cell[1][2][4].
Related Catalog
In Vitro (E)-Naringenin chalcone (25-125 μg/mL, 10 min) inhibits histamine release from rat peritoneal mast cells, with an IC50 value of 68 μg/mL[1]. (E)-Naringenin chalcone (25-50 μM, 8 days) improves adipocyte (3T3-L1) functions by enhancing adiponectin production[2]. (E)-Naringenin chalcone (25-100 μM, 24 h) stimulates the activity of PPARγ in NIH-3T3 cells[2]. (E)-Naringenin chalcone (0-200 μM 24 h) inhibits the production of TNF-alpha, MCP-1, and nitric oxide (NO) by LPS-stimulated RAW 264 macrophages[4]. RT-PCR[2] Cell Line: 3T3-L1 adipocytes Concentration: 25-100 μM Incubation Time: 8 days Result: Increased adiponectin mRNA levels up to 8.0-fold in a dose-dependent manner. Western Blot Analysis[4] Cell Line: RAW 264 macrophages Concentration: 0,25, 50, 100, 200 μM Incubation Time: 24 h Result: Suppressed the degradation of IκB-α.
In Vivo (E)-Naringenin chalcone (0.8 mg/kg, oral administration) shows anti-allergic effect in type I allergic mice[1]. (E)-Naringenin chalcone (0.8 mg/kg, oral administration) suppresses allergic asthma by inhibiting the type-2 function of CD4 T cells in allergic airway inflammatory mice[3]. Animal Model: Mouse type I allergic model[1] Dosage: 0.8 mg/kg Administration: Oral administration Result: Inhibited the ear-swelling response, with the inhibitory ratio of 46.7%. Animal Model: Allergic airway inflammation induced in mice[3] Dosage: 0.8 mg/kg Administration: Oral administration, daily Result: Decreased cell numbers of the infiltrating leukocyte and eosinophils. Decreased Muc5ac and gob-5 expression in the lungs.
References

[1]. Taichi Yamamoto, et al. Anti-allergic activity of naringenin chalcone from a tomato skin extract. Biosci Biotechnol Biochem. 2004 Aug;68(8):1706-11.

[2]. Taro Horiba, et al. Naringenin chalcone improves adipocyte functions by enhancing adiponectin production. Mol Cell Endocrinol. 2010 Jul 29;323(2):208-14.

[3]. Chiaki Iwamura, et al. Naringenin chalcone suppresses allergic asthma by inhibiting the type-2 function of CD4 T cells. Allergol Int. 2010 Mar;59(1):67-73.

[4]. Shizuka Hirai, et al. Inhibitory effect of naringenin chalcone on inflammatory changes in the interaction between adipocytes and macrophages. Life Sci. 2007 Sep 29;81(16):1272-9.

 Chemical & Physical Properties

Density 1.483±0.06 g/cm3(Predicted)
Boiling Point 538.7±50.0 °C(Predicted)
Molecular Formula C15H12O5
Molecular Weight 272.25300
Exact Mass 272.06800
PSA 97.99000
LogP 2.40510
Storage condition 2-8°C

 Synthetic Route

~80%

2',4,4',6'-TETRAHYDROXYCHALCONE Structure

2',4,4',6'-TETR...

CAS#:25515-46-2

Literature: Stompor, Monika; Potaniec, Bartomiej; Szumny, Antoni; Zielinski, Pawe; Zonierczyk, Anna Katarzyna; Aniol, Miroslaw Journal of Molecular Catalysis B: Enzymatic, 2013 , vol. 97, p. 283 - 288

~%

2',4,4',6'-TETRAHYDROXYCHALCONE Structure

2',4,4',6'-TETR...

CAS#:25515-46-2

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

~%

2',4,4',6'-TETRAHYDROXYCHALCONE Structure

2',4,4',6'-TETR...

CAS#:25515-46-2

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

~%

2',4,4',6'-TETRAHYDROXYCHALCONE Structure

2',4,4',6'-TETR...

CAS#:25515-46-2

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

~%

2',4,4',6'-TETRAHYDROXYCHALCONE Structure

2',4,4',6'-TETR...

CAS#:25515-46-2

Literature: Abe, Ikuro; Oguro, Satoshi; Utsumi, Yoriko; Sano, Yukie; Noguchi, Hiroshi Journal of the American Chemical Society, 2005 , vol. 127, # 36 p. 12709 - 12716

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2',4,4',6'-TETRAHYDROXYCHALCONE Structure

2',4,4',6'-TETR...

CAS#:25515-46-2

Literature: Kenez, Agnes; Juhasz, Laszlo; Antus, Sandor Heterocyclic Communications, 2002 , vol. 8, # 6 p. 543 - 548

~%

2',4,4',6'-TETRAHYDROXYCHALCONE Structure

2',4,4',6'-TETR...

CAS#:25515-46-2

Literature: Kenez, Agnes; Juhasz, Laszlo; Antus, Sandor Heterocyclic Communications, 2002 , vol. 8, # 6 p. 543 - 548

~%

2',4,4',6'-TETRAHYDROXYCHALCONE Structure

2',4,4',6'-TETR...

CAS#:25515-46-2

Literature: Abe, Tsuyoshi; Noma, Hisashi; Noguchi, Hiroshi; Abe, Ikuro Tetrahedron Letters, 2006 , vol. 47, # 49 p. 8727 - 8730

 Synonyms

Isopropylammonium-N-isopropyl-dithiocarbaminat
isorpopylammonium N-isopropyldithiocarbamate
propan-2-ylcarbamodithioic acid
isosalipurpol
trans-2',4',6',4-tetrahydroxychalcone
chalconaringenin
6',4-tetrahydroxychalcone
isopropylammonium N-isopropyldithiocarbamate
ammonium isopropyldithiocarbamate
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