Retusin

CAS# 1245-15-4

Retusin

2D Structure

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Quality Control of Retusin

3D structure

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Retusin

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Chemical Properties of Retusin

Cas No. 1245-15-4 SDF Download SDF
PubChem ID 5352005 Appearance Yellow powder
Formula C19H18O7 M.Wt 358.34
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms 480-86-4;Retusine
Solubility Soluble in methan
Chemical Name 2-(3,4-dimethoxyphenyl)-5-hydroxy-3,7-dimethoxychromen-4-one
SMILES COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)OC)O)OC)OC
Standard InChIKey HHGPYJLEJGNWJA-UHFFFAOYSA-N
Standard InChI InChI=1S/C19H18O7/c1-22-11-8-12(20)16-15(9-11)26-18(19(25-4)17(16)21)10-5-6-13(23-2)14(7-10)24-3/h5-9,20H,1-4H3
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 Retusin

1 Geranium sp. 2 Pterocarpus sp.

Biological Activity of Retusin

Description1. Retusin behaves as pre- and postemergent herbicides. 2. Retusin exhibits potent free-radical-scavenging capacities as well as efficient inhibition of cellular melanogenesis. 3. Retusin is a weak inhibitor of ATP synthesis.
TargetsTyrosinase

Retusin Dilution Calculator

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Retusin Molarity Calculator

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Preparing Stock Solutions of Retusin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.7906 mL 13.9532 mL 27.9065 mL 55.8129 mL 69.7661 mL
5 mM 0.5581 mL 2.7906 mL 5.5813 mL 11.1626 mL 13.9532 mL
10 mM 0.2791 mL 1.3953 mL 2.7906 mL 5.5813 mL 6.9766 mL
50 mM 0.0558 mL 0.2791 mL 0.5581 mL 1.1163 mL 1.3953 mL
100 mM 0.0279 mL 0.1395 mL 0.2791 mL 0.5581 mL 0.6977 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 Retusin

Free-Radical-Scavenging, Antityrosinase, and Cellular Melanogenesis Inhibitory Activities of Synthetic Isoflavones.[Pubmed:26080742]

Chem Biodivers. 2015 Jun;12(6):963-79.

In this study, we examined the potential of synthetic isoflavones for application in cosmeceuticals. Twenty-five isoflavones were synthesized and their capacities of free-radical-scavenging and mushroom tyrosinase inhibition, as well as their impact on cell viability of B16F10 murine melanoma cells and HaCaT human keratinocytes were evaluated. Isoflavones that showed significant mushroom tyrosinase inhibitory activities were further studied on reduction of cellular melanin formation and antityrosinase activities in B16F10 melanocytes in vitro. Among the isoflavones tested, 6-hydroxydaidzein (2) was the strongest scavenger of both ABTS(.+) and DPPH(.) radicals with SC50 values of 11.3 +/- 0.3 and 9.4 +/- 0.1 muM, respectively. Texasin (20) exhibited the most potent inhibition of mushroom tyrosinase (IC50 14.9 +/- 4.5 muM), whereas Retusin (17) showed the most efficient inhibition both of cellular melanin formation and antityrosinase activity in B16F10 melanocytes, respectively. In summary, both Retusin (17) and texasin (20) exhibited potent free-radical-scavenging capacities as well as efficient inhibition of cellular melanogenesis, suggesting that they are valuable hit compounds with potential for advanced cosmeceutical development.

Flavonoids Affect the Light Reaction of Photosynthesis in Vitro and in Vivo as Well as the Growth of Plants.[Pubmed:26322527]

J Agric Food Chem. 2015 Sep 23;63(37):8106-15.

Flavonoids Retusin (5-hydroxy-3,7,3',4'-tetramethoxyflavone) (1) and pachypodol (5,4'-dihydroxy-3,7,3'-trimethoxyflavone) (2) were isolated from Croton ciliatoglanduliferus Ort. Pachypodol acts as a Hill reaction inhibitor with its target on the water splitting enzyme located in PSII. In the search for new herbicides from natural compounds, flavonoids 1 and 2 and flavonoid analogues quercetin (3), apigenin (4), genistein (5), and eupatorin (6) were assessed for their effect in vitro on the photosynthetic electron transport chain and in vivo on the germination and growth of the plants Physalis ixocarpa, Trifolium alexandrinum and Lolium perenne. Flavonoid 3 was the most active inhibitor of the photosynthetic uncoupled electron flow (I50 = 114 muM) with a lower log P value (1.37). Results in vivo suggest that 1, 2, 3, and 5 behave as pre- and postemergent herbicides, with 3 and 5 being more active.

Pachypodol from Croton ciliatoglanduliferus Ort. as water-splitting enzyme inhibitor on thylakoids.[Pubmed:16478239]

J Agric Food Chem. 2006 Feb 22;54(4):1217-21.

A bioactivity-guided chemical study of aerial parts of Croton ciliatoglanduliferus Ort. led to the isolation for the first time of the flavonoids Retusin (5-hydroxy-3,7,3',4'-tetramethoxyflavone) (1) and pachypodol (5,4'-dihydroxy-3,7,3'-trimethoxyflavone) (2) from the n-hexane extract. Compounds 1 and 2 were separated by preparative thin-layer chromatography. Compound 2 was the most active compound on ATP synthesis inhibition. The I50 value was 51 microM. Pachypodol behaves as a Hill reaction inhibitor. It inhibited the uncoupled electron flow on photosystem II partial reaction from water to dichlorophenol indophenol (DCPIP) and from water to sodium silicomolybdate. However, the uncoupled partial reaction from diphenylcarbazide to DCPIP and the uncoupled photosystem I from DCPIPred to MV were not inhibited by 2. These results were corroborated by fluorescence decay data. Therefore, pachypodol inhibits the water-splitting enzyme activity. Compound 1 with a 4'-methoxy group was a weak inhibitor, indicating that the 4' free -OH group is important for strong inhibition.

Description

Retusin (Quercetin-3,3',4',7-tetramethylether), a natural compound isolated from the leaves of Talinum triangulare, possesses antiviral and anti-inflammatory activities.

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