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2,5-Dihydroxyacetophenone

CAS# 490-78-8

2,5-Dihydroxyacetophenone

2D Structure

Catalog No. BCN3825----Order now to get a substantial discount!

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Quality Control of 2,5-Dihydroxyacetophenone

3D structure

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2,5-Dihydroxyacetophenone

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Chemical Properties of 2,5-Dihydroxyacetophenone

Cas No. 490-78-8 SDF Download SDF
PubChem ID 10279 Appearance Powder
Formula C8H8O3 M.Wt 152.2
Type of Compound Phenols Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 1-(2,5-dihydroxyphenyl)ethanone
SMILES CC(=O)C1=C(C=CC(=C1)O)O
Standard InChIKey WLDWSGZHNBANIO-UHFFFAOYSA-N
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of 2,5-Dihydroxyacetophenone

The fruits of Citrus maxima

Biological Activity of 2,5-Dihydroxyacetophenone

Description2,5-Dihydroxyacetophenone is an uncompetitive inhibitor of murine tyrosinase (K(I) 0.28mm), it strongly inhibits both melanogenesis and cellular tyrosinase activity, it possesses anti-inflammatoryanti-anxiety, and neuroprotective qualities. 2,5-Dihydroxyacetophenone treatment can induce a sustained activation of JNK, ERK1/2, and p38 MAPKs, it also can potentiate the pro-apoptotic and anti-proliferative effects of bortezomib in U266 cells.
TargetsJNK | ERK | p38MAPK | p21 | Bcl-2/Bax | COX | MMP(e.g.TIMP) | NF-kB | Tyrosinase
In vitro

2,5-dihydroxyacetophenone isolated from Rehmanniae Radix Preparata inhibits inflammatory responses in lipopolysaccharide-stimulated RAW264.7 macrophages.[Pubmed: 22510152 ]

J Med Food. 2012 Jun;15(6):505-10.

Rehmanniae Radix Preparata, the steamed root of Rehmannia glutinosa Libosch, has been widely used for the treatment of inflammatory conditions in Oriental medicines.
METHODS AND RESULTS:
In this study we evaluated the effects of 2,5-Dihydroxyacetophenone (DHAP) isolated from Rehmanniae Radix Preparata on inflammatory responses in lipopolysaccharide (LPS)-stimulated RAW264.7 mouse macrophages. LPS-stimulated RAW264.7 cells were used to investigate the anti-inflammatory activity of DHAP on the production of inflammatory mediators such as nitric oxide (NO), inducible NO synthase (iNOS), tumor necrosis factor-α (TNF-α), and interleukin (IL)-6. DHAP significantly inhibited NO production via the suppression of iNOS expression and significantly decreased levels of the pro-inflammatory cytokines TNF-α and IL-6 via the down-regulation of their mRNA expression in LPS-stimulated RAW264.7 cells. DHAP potently inhibited the phosphorylation of extracellular signal-related kinase (ERK) 1/2 and the nuclear translocation of nuclear factor-κB (NF-κB) p65 in LPS-stimulated cells. These results indicate that DHAP inhibits the production of inflammatory mediators in activated macrophages by blocking the ERK1/2 and NF-κB signaling pathways.
CONCLUSIONS:
Our results suggest that DHAP from Rehmanniae Radix Preparata has anti-inflammatory activity in activated macrophages, raising the possibility that this compound has a therapeutic potential for inflammatory conditions.

In vivo

Murine tyrosinase inhibitors from Cynanchum bungei and evaluation of in vitro and in vivo depigmenting activity.[Pubmed: 21615508]

Exp Dermatol. 2011 Sep;20(9):720-4.


METHODS AND RESULTS:
Two natural acetophenone derivatives, 2,5-Dihydroxyacetophenone (2,5-DHAP) and 2,6-DHAP, were purified from Cynanchum bungei and identified as murine tyrosinase inhibitors. Investigation into 2,5-DHAP showed it to be an uncompetitive inhibitor of murine tyrosinase (K(I) 0.28 mm). 2,5-DHAP strongly inhibited both melanogenesis and cellular tyrosinase activity in vitro in 3-isobutyl-1-methylxanthin-stimulated B16 mouse melanoma cells or in vivo in zebrafish and mouse models, but showed no cytotoxicity at the concentrations used. In B16 cells, 2,5-DHAP inhibition was dose-dependent and was fourfold greater than that of arbutin. 2,5-DHAP had no effect on the expression of tyrosinase protein or mRNA, as confirmed by Western blotting and quantitative real-time reverse transcription polymerase chain reaction, respectively.
CONCLUSIONS:
A 2% gel preparation of 2,5-DHAP applied to the skin of mice significantly increased the average skin-whitening index (L value), indicating its potential use as a treatment for skin hyperpigmentation in humans.

Protocol of 2,5-Dihydroxyacetophenone

Kinase Assay

2,5-Dihydroxyacetophenone Induces Apoptosis of Multiple Myeloma Cells by Regulating the MAPK Activation Pathway.[Pubmed: 28696369 ]

Molecules. 2017 Jul 11;22(7).

2,5-Dihydroxyacetophenone (DHAP) is an active compound obtained from Radix rehmanniae preparata, which is widely used as a herbal medicine in many Asian countries. DHAP has been found to possess anti-inflammatory, anti-anxiety, and neuroprotective qualities.
METHODS AND RESULTS:
For the present study, we evaluated the anti-cancer effects of DHAP on multiple myeloma cells. It was discovered that DHAP downregulated the expression of oncogenic gene products like Bcl-xl, Bcl-2, Mcl-1, Survivin, Cyclin D1, IAP-1, Cyclin E, COX-2, and MMP-9, and upregulated the expression of Bax and p21 proteins, consistent with the induction of G2/M phase cell cycle arrest and apoptosis in U266 cells. We therefore attempted to determine the effect of DHAP on MAPK signaling pathways, and discovered that DHAP treatment induced a sustained activation of JNK, ERK1/2, and p38 MAPKs. DHAP also potentiated the pro-apoptotic and anti-proliferative effects of bortezomib in U266 cells.
CONCLUSIONS:
Our results suggest that DHAP can be an effective therapeutic agent to target multiple myeloma.

2,5-Dihydroxyacetophenone Dilution Calculator

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Preparing Stock Solutions of 2,5-Dihydroxyacetophenone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 6.5703 mL 32.8515 mL 65.703 mL 131.406 mL 164.2576 mL
5 mM 1.3141 mL 6.5703 mL 13.1406 mL 26.2812 mL 32.8515 mL
10 mM 0.657 mL 3.2852 mL 6.5703 mL 13.1406 mL 16.4258 mL
50 mM 0.1314 mL 0.657 mL 1.3141 mL 2.6281 mL 3.2852 mL
100 mM 0.0657 mL 0.3285 mL 0.657 mL 1.3141 mL 1.6426 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on 2,5-Dihydroxyacetophenone

2,5-dihydroxyacetophenone isolated from Rehmanniae Radix Preparata inhibits inflammatory responses in lipopolysaccharide-stimulated RAW264.7 macrophages.[Pubmed:22510152]

J Med Food. 2012 Jun;15(6):505-10.

Rehmanniae Radix Preparata, the steamed root of Rehmannia glutinosa Libosch, has been widely used for the treatment of inflammatory conditions in Oriental medicines. In this study we evaluated the effects of 2,5-Dihydroxyacetophenone (DHAP) isolated from Rehmanniae Radix Preparata on inflammatory responses in lipopolysaccharide (LPS)-stimulated RAW264.7 mouse macrophages. LPS-stimulated RAW264.7 cells were used to investigate the anti-inflammatory activity of DHAP on the production of inflammatory mediators such as nitric oxide (NO), inducible NO synthase (iNOS), tumor necrosis factor-alpha (TNF-alpha), and interleukin (IL)-6. DHAP significantly inhibited NO production via the suppression of iNOS expression and significantly decreased levels of the pro-inflammatory cytokines TNF-alpha and IL-6 via the down-regulation of their mRNA expression in LPS-stimulated RAW264.7 cells. DHAP potently inhibited the phosphorylation of extracellular signal-related kinase (ERK) 1/2 and the nuclear translocation of nuclear factor-kappaB (NF-kappaB) p65 in LPS-stimulated cells. These results indicate that DHAP inhibits the production of inflammatory mediators in activated macrophages by blocking the ERK1/2 and NF-kappaB signaling pathways. Our results suggest that DHAP from Rehmanniae Radix Preparata has anti-inflammatory activity in activated macrophages, raising the possibility that this compound has a therapeutic potential for inflammatory conditions.

2,5-Dihydroxyacetophenone Induces Apoptosis of Multiple Myeloma Cells by Regulating the MAPK Activation Pathway.[Pubmed:28696369]

Molecules. 2017 Jul 11;22(7). pii: molecules22071157.

2,5-Dihydroxyacetophenone (DHAP) is an active compound obtained from Radix rehmanniae preparata, which is widely used as a herbal medicine in many Asian countries. DHAP has been found to possess anti-inflammatory, anti-anxiety, and neuroprotective qualities. For the present study, we evaluated the anti-cancer effects of DHAP on multiple myeloma cells. It was discovered that DHAP downregulated the expression of oncogenic gene products like Bcl-xl, Bcl-2, Mcl-1, Survivin, Cyclin D1, IAP-1, Cyclin E, COX-2, and MMP-9, and upregulated the expression of Bax and p21 proteins, consistent with the induction of G2/M phase cell cycle arrest and apoptosis in U266 cells. DHAP inhibited cell proliferation and induced apoptosis, as characterized by the cleavage of PARP and the activation of caspase-3, caspase-8, and caspase-9. Mitogen-activated protein kinase (MAPK) pathways have been linked to the modulation of the angiogenesis, proliferation, metastasis, and invasion of tumors. We therefore attempted to determine the effect of DHAP on MAPK signaling pathways, and discovered that DHAP treatment induced a sustained activation of JNK, ERK1/2, and p38 MAPKs. DHAP also potentiated the pro-apoptotic and anti-proliferative effects of bortezomib in U266 cells. Our results suggest that DHAP can be an effective therapeutic agent to target multiple myeloma.

Murine tyrosinase inhibitors from Cynanchum bungei and evaluation of in vitro and in vivo depigmenting activity.[Pubmed:21615508]

Exp Dermatol. 2011 Sep;20(9):720-4.

Two natural acetophenone derivatives, 2,5-Dihydroxyacetophenone (2,5-DHAP) and 2,6-DHAP, were purified from Cynanchum bungei and identified as murine tyrosinase inhibitors. Investigation into 2,5-DHAP showed it to be an uncompetitive inhibitor of murine tyrosinase (K(I) 0.28 mm). 2,5-DHAP strongly inhibited both melanogenesis and cellular tyrosinase activity in vitro in 3-isobutyl-1-methylxanthin-stimulated B16 mouse melanoma cells or in vivo in zebrafish and mouse models, but showed no cytotoxicity at the concentrations used. In B16 cells, 2,5-DHAP inhibition was dose-dependent and was fourfold greater than that of arbutin. 2,5-DHAP had no effect on the expression of tyrosinase protein or mRNA, as confirmed by Western blotting and quantitative real-time reverse transcription polymerase chain reaction, respectively. A 2% gel preparation of 2,5-DHAP applied to the skin of mice significantly increased the average skin-whitening index (L value), indicating its potential use as a treatment for skin hyperpigmentation in humans.

Description

2,5-Dihydroxyacetophenone, isolated from Rehmanniae Radix Preparata, inhibits the production of inflammatory mediators in activated macrophages by blocking the ERK1/2 and NF-κB signaling pathways.

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