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(S)-4-Methoxydalbergione

CAS# 2543-95-5

(S)-4-Methoxydalbergione

Catalog No. BCN9627----Order now to get a substantial discount!

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Chemical structure

(S)-4-Methoxydalbergione

3D structure

Chemical Properties of (S)-4-Methoxydalbergione

Cas No. 2543-95-5 SDF Download SDF
PubChem ID 10400054 Appearance Yellow cryst.
Formula C16H14O3 M.Wt 254.28
Type of Compound Other Quinones Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 2-methoxy-5-[(1S)-1-phenylprop-2-enyl]cyclohexa-2,5-diene-1,4-dione
SMILES COC1=CC(=O)C(=CC1=O)C(C=C)C2=CC=CC=C2
Standard InChIKey RGSUZUQISVAJJF-LBPRGKRZSA-N
Standard InChI InChI=1S/C16H14O3/c1-3-12(11-7-5-4-6-8-11)13-9-15(18)16(19-2)10-14(13)17/h3-10,12H,1H2,2H3/t12-/m0/s1
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.

(S)-4-Methoxydalbergione Dilution Calculator

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Preparing Stock Solutions of (S)-4-Methoxydalbergione

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.9327 mL 19.6634 mL 39.3267 mL 78.6535 mL 98.3168 mL
5 mM 0.7865 mL 3.9327 mL 7.8653 mL 15.7307 mL 19.6634 mL
10 mM 0.3933 mL 1.9663 mL 3.9327 mL 7.8653 mL 9.8317 mL
50 mM 0.0787 mL 0.3933 mL 0.7865 mL 1.5731 mL 1.9663 mL
100 mM 0.0393 mL 0.1966 mL 0.3933 mL 0.7865 mL 0.9832 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 (S)-4-Methoxydalbergione

Contact dermatitis of the lips due to late-type sensitization against dalbergiones in a wooden recorder.[Pubmed:31826027]

Allergol Select. 2018 Sep 1;2(1):29-31.

BACKGROUND: Late-type sensitizations against wood are rare and are mostly seen in patients with occupational contact with saw dust. Generally, commercial wooden products only lead to sensitization or dermatitis in cases when contact to the unprotected skin is direct, intensive and of longer duration, i.e. by wearing wooden jewelry or by playing wooden instruments. Causative for the sensitization process are ingredients of the wood core such as alkaloids, glycosides, anthrachinones, saponines, phenols, catechols, flavonoids, cumarins, and benzo-, naphtho-, furano-, and phenanthrenquinones and their precursors. CASE REPORT: We report the case of a 70-year-old patient who developed cheilitis after playing different wooden recorders made of African blackwood, rosewood, cedar, olive, and pear. METHODS: Patch testing with baseline series of contact allergens and saw dust of the recorders were performed as well as skin prick tests with common inhalant allergens and saw dust of the recorders. RESULTS: Patch testing showed sensitizations against African blackwood, rosewood, fragrance mix 2 and hydroxyisohexyl-3-cyclohexene carboxaldehyde. Skin prick testing was without pathological results. CONCLUSION: African blackwood and rosewood contain (S)-4'-hydroxy-4-methoxydalbergione and (S)-4-Methoxydalbergione. As a result of the chemical affinity between the dalbergiones, cross-reactions between different woods are observed. The case presented shall show the diagnostic procedure in cases in which sensitizations against wood components are suspected.

Catalytic asymmetric addition of Meldrum's acid, malononitrile, and 1,3-dicarbonyls to ortho-quinone methides generated in situ under basic conditions.[Pubmed:25766504]

Chemistry. 2015 Apr 13;21(16):6037-41.

A new approach to the utilization of highly reactive and unstable ortho-quinone methides (o-QMs) in catalytic asymmetric settings is presented. The enantioselective reactions are catalysed by bifunctional organocatalysts, and the o-QM intermediates are formed in situ from 2-sulfonylalkyl phenols through base-promoted elimination of sulfinic acid. The use of mild Bronsted basic conditions for transiently generating o-QMs in catalytic asymmetric processes is unprecedented, and allows engaging productively in the reactions nucleophiles such as Meldrum's acid, malononitrile and 1,3-dicarbonyls. The catalytic transformations give new and general entries to 3,4-dihydrocoumarins, 4H-chromenes and xanthenones. These frameworks are recurring structures in natural product and medicinal chemistry, as testified by the formal syntheses of (R)-tolterodine and (S)-4-Methoxydalbergione from the catalytic adducts.

Enantioselective addition of boronates to o-quinone methides catalyzed by chiral biphenols.[Pubmed:23206197]

J Am Chem Soc. 2012 Dec 12;134(49):19965-8.

Chiral biphenols were found to catalyze the enantioselective asymmetric addition of aryl- or alkenylboronates to o-quinone methides. Substituted 2-styryl phenols were obtained in good yields (up to 95%) with high enantiomeric ratios (up to 98:2) in the presence of 10 mol % 3,3'-Br(2)-BINOL. A two-step synthesis of (S)-4-Methoxydalbergione in good yield and selectivity was achieved.

Three new flavonoids and antiallergic, anti-inflammatory constituents from the heartwood of Dalbergia odorifera.[Pubmed:9525107]

Planta Med. 1998 Mar;64(2):153-8.

Three new flavonoids, (3R)-4'-methoxy-2',3,7-trihydroxyisoflavanone (11), 7-methoxy-3,3',4',6-tetrahydroxyflavone (18), and 2',7-dihydroxy-4',5'-dimethoxyisoflavone (22), were isolated from the heartwood of Dalbergia odorifera T. Chen. (Leguminosae), together with twenty-two known compounds, (S)-4-Methoxydalbergione (1), cearoin (2), medicarpin (3), formononetin (4), sativanone (5), 3-hydroxy-9-methoxy-coumestan (6), meliotocarpan A (7), isoliquiritigenin (8), stevein (9), liquiritigenin (10), 3',4',7-trihydroxyflavanone (12), butein (13), 3'-hydroxymelanettin (14), koparin (15), bowdichione (16), fisetin (17), melanettin (19), sulfuretin (20), 3'-hydroxydaidzein (21), 3'-O-methylviolanone (23), xenognosin B (24), and dalbergin (25). These flavonoids were evaluated in antiallergic and anti-inflammatory tests. The results showed that (S)-4-Methoxydalbergione (1) and cearoin (2) exhibited antiallergic activity while (S)-4-Methoxydalbergione (1), cearoin (2), butein (13), koparin (15), bowdichione (16), 3'-O-methylviolanone (23), and xenognosin B (24) showed significant anti-inflammatory activity.

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