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Dihydromollugin

CAS# 60657-93-4

Dihydromollugin

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Chemical structure

Dihydromollugin

3D structure

Chemical Properties of Dihydromollugin

Cas No. 60657-93-4 SDF Download SDF
PubChem ID 10779560 Appearance Powder
Formula C17H18O4 M.Wt 286.32
Type of Compound Quinones Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name methyl 6-hydroxy-2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5-carboxylate
SMILES CC1(CCC2=C(O1)C3=CC=CC=C3C(=C2C(=O)OC)O)C
Standard InChIKey AKPYYGWMASCNAF-UHFFFAOYSA-N
Standard InChI InChI=1S/C17H18O4/c1-17(2)9-8-12-13(16(19)20-3)14(18)10-6-4-5-7-11(10)15(12)21-17/h4-7,18H,8-9H2,1-3H3
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 Dihydromollugin

The roots of Rubia cordifolia L.

Protocol of Dihydromollugin

Structure Identification
Phytochemistry, 28(12):3465-3468.

Anthraquinones and naphthohydroquinones from Rubia cordifolia.[Reference: WebLink]


METHODS AND RESULTS:
Four naphthohydroquinones and their glycosides, and 11 anthraquinones and their glycosides were isolated from the dried roots of Rubia cordifolia var. pratensis. Six of them, Dihydromollugin, 2-carbomethoxy-3-(3′- hydroxy)isopentyl-1,4-naphthohydroquinone 4-O-β-glucoside, 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone 3-O-β-glucoside, 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone 3-O-(3′-O-acetyl)-α-rhamnosyl (1→2)-β-glucoside, 2-methyl- 1,3,6-trihydroxy-9,10-anthraquinone 3-O-(3′,6′-O-diacetyl)-α-rhamnosyl(1→2)-β-glucoside and 2-methyl-1,3,6-tri- hydroxy-9,10-anthraquinone 3-O-(4′,6′-O-diacetyl)-α-rhamnosyl(1→2)-β-glucoside, were isolated for the first time from a natural source.
CONCLUSIONS:
The structures were established by various chemical and spectroscopic methods. The chemotaxonomic significance of these findings is discussed briefly.

Journal of the Chinese Chemical Society, 2001,48(1):77-79.

Synthesis of Naturally Occurring Rubilactone, Mollugin, and Dihydromollugin of Rubia cordifolia.[Reference: WebLink]

Rubilactone (1), Dihydromollugin (2), and mollugin (3) are naturally occurring products found in Rubia cordifolia, which is a famous Chinese herb with anti tumor, viral inhibition and other activities. Synthetic studies were carried out in these naphthoic acid esters starting from 1,4-dihydroxy-2-naphthoic acid.
METHODS AND RESULTS:
In this study, we finished the synthesis of rubilactone which has not been reported before and also synthesized Dihydromollugin and mollugin with better yields with different approaches compared to those previously reported in the literature.

Dihydromollugin Dilution Calculator

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Preparing Stock Solutions of Dihydromollugin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.4926 mL 17.463 mL 34.926 mL 69.8519 mL 87.3149 mL
5 mM 0.6985 mL 3.4926 mL 6.9852 mL 13.9704 mL 17.463 mL
10 mM 0.3493 mL 1.7463 mL 3.4926 mL 6.9852 mL 8.7315 mL
50 mM 0.0699 mL 0.3493 mL 0.6985 mL 1.397 mL 1.7463 mL
100 mM 0.0349 mL 0.1746 mL 0.3493 mL 0.6985 mL 0.8731 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 Dihydromollugin

Efficient synthesis of cis- and trans-3,4-dihydroxy-3,4-dihydromollugin.[Pubmed:18412388]

J Org Chem. 2008 May 16;73(10):3867-74.

An efficient synthesis of naturally occurring compounds isolated from Pentas longiflora, cis-3,4-dihydroxy-3,4-Dihydromollugin 2, and trans-3,4-dihydroxy-3,4-Dihydromollugin 3 is described. The O-protected mollugins were dihydroxylated using OsO4 to achieve the corresponding cis-dihydroxy derivatives in excellent yield. The synthesis of trans-3,4-dihydroxy-3,4-Dihydromollugin was achieved using Oxone in good yield. A mechanism for the formation of cis-3,4-dihydroxymollugin acetonide from the reaction of mollugin with Oxone is proposed.

New pyranonaphthoquinone and pyranonaphthohydroquinone from the roots of Pentas longiflora.[Pubmed:12350172]

J Nat Prod. 2002 Sep;65(9):1377-9.

Several quinone type compounds were isolated from the hexane, dichloromethane, and ethyl acetate extracts of the roots of Pentas longiflora. The hexane extract afforded two new compounds, [(3alpha,3'alpha,4beta,4'beta)-3,3']-dimethoxy-cis-[4,4'-bis(3,4,5,10-tetrahydro- 1H-naphtho[2,3-c]pyran)]-5,5',10,10'-tetraone (1) and cis-3,4-dihydroxy-3,4-Dihydromollugin (2), together with six known compounds, namely, pentalongin, mollugin, trans-3,4-dihydroxy-3,4-Dihydromollugin, methyl-2,3-epoxy-3-prenyl-1,4-naphthoquinone-2-carboxylate, tectoquinone, and 3-hydroxymollugin. From the dichloromethane extract were isolated the three known compounds 3-methoxymollugin, methyl-3-prenyl-1,4-naphthoquinone-2-carboxylate, and scopoletin, while the ethyl acetate extract afforded the known 2-methoxy-3-methylanthraquinone.

[Studies on naphthoic acid esters from the roots of Rubia cordifolia L].[Pubmed:1442042]

Yao Xue Xue Bao. 1992;27(4):279-82.

Four naphthoic acid esters including a new compound were isolated from the roots of Rubia cordifolia L. The new one was named as rubilactone and its structure was elucidated as 3'-carbomethoxy-4'-hydroxy-naphtho[1',2'-2,3] pyran-6-one (I) based on the physicochemical properties and spectrometric analyses (UV, IR, MS, 1HNMR and 13CNMR). The other three were 3'-carbomethoxy-4'-hydroxy-naphtho [1',2'-2,3] furan (II), Dihydromollugin (III) and 3-carbomethoxy-2-(3'-hydroxy)isopentyl-1,4-naphthohydroquinone-1-O -beta-D-glucoside (IV).

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