Beta-Rotunol

CAS# 24405-57-0

Beta-Rotunol

Catalog No. BCN6628----Order now to get a substantial discount!

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Beta-Rotunol: 5mg $828 In Stock
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Quality Control of Beta-Rotunol

Number of papers citing our products

Chemical structure

Beta-Rotunol

3D structure

Chemical Properties of Beta-Rotunol

Cas No. 24405-57-0 SDF Download SDF
PubChem ID 5321005 Appearance Powder
Formula C15H22O2 M.Wt 234.3
Type of Compound Sesquiterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (4aR,6R,8aS)-4a-hydroxy-4,8a-dimethyl-6-prop-1-en-2-yl-5,6,7,8-tetrahydro-1H-naphthalen-2-one
SMILES CC1=CC(=O)CC2(C1(CC(CC2)C(=C)C)O)C
Standard InChIKey WDFLKCAWQQMJCA-SNPRPXQTSA-N
Standard InChI InChI=1S/C15H22O2/c1-10(2)12-5-6-14(4)9-13(16)7-11(3)15(14,17)8-12/h7,12,17H,1,5-6,8-9H2,2-4H3/t12-,14+,15+/m1/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.

Source of Beta-Rotunol

The herbs of Cyperus rotundus.

Biological Activity of Beta-Rotunol

DescriptionStandard reference

Protocol of Beta-Rotunol

Structure Identification
Tetrahedron,1971, 27(19):4831-6.

Structure and absolute configuration of α-rotunol and β-rotunol, sesquiterpenoids of Cyperus rotundus.[Reference: WebLink]


METHODS AND RESULTS:
Two novel sesquiterpenic keto-alcohols, α-rotunol and β-rotunol(Beta-Rotunol), have been isolated from nutgrass, Cyperus rotundus ;Cyperaceae). The stereostructure II of β-rotunol is based on spectral properties and by transformation to the dienone (V) which has also been derived from hinesol (VI). α-Rotunol has been given the stereostructure I based on its physico-chemical properties.

Beta-Rotunol Dilution Calculator

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Beta-Rotunol Molarity Calculator

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Preparing Stock Solutions of Beta-Rotunol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.268 mL 21.3402 mL 42.6803 mL 85.3606 mL 106.7008 mL
5 mM 0.8536 mL 4.268 mL 8.5361 mL 17.0721 mL 21.3402 mL
10 mM 0.4268 mL 2.134 mL 4.268 mL 8.5361 mL 10.6701 mL
50 mM 0.0854 mL 0.4268 mL 0.8536 mL 1.7072 mL 2.134 mL
100 mM 0.0427 mL 0.2134 mL 0.4268 mL 0.8536 mL 1.067 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 Beta-Rotunol

Anti-inflammatory components from the root of Solanum erianthum.[Pubmed:23771024]

Int J Mol Sci. 2013 Jun 14;14(6):12581-92.

Two new norsesquiterpenoids, solanerianones A and B (1-2), together with nine known compounds, including four sesquiterpenoids, (-)-solavetivone (3), (+)-anhydro-Beta-Rotunol (4), solafuranone (5), lycifuranone A (6); one alkaloid, N-trans-feruloyltyramine (7); one fatty acid, palmitic acid (8); one phenylalkanoid, acetovanillone (9), and two steroids, beta-sitosterol (10) and stigmasterol (11) were isolated from the n-hexane-soluble part of the roots of Solanum erianthum. Their structures were elucidated on the basis of physical and spectroscopic data analyses. The anti-inflammatory activity of these isolates was monitored by nitric oxide (NO) production in lipopolysaccharide (LPS)-activated murine macrophage RAW264.7 cells. The cytotoxicity towards human lung squamous carcinoma (CH27), human hepatocellular carcinoma (Hep 3B), human oral squamous carcinoma (HSC-3) and human melanoma (M21) cell lines was also screened by using an MTT assay. Of the compounds tested, 3 exhibited the strongest NO inhibition with the average maximum inhibition (Emax) at 100 muM and median inhibitory concentration (IC50) values of 98.23% +/- 0.08% and 65.54 +/- 0.18 muM, respectively. None of compounds (1-9) was found to possess cytotoxic activity against human cancer cell lines at concentrations up to 30 muM.

Kandenols A-E, eudesmenes from an endophytic Streptomyces sp. of the mangrove tree Kandelia candel.[Pubmed:23234344]

J Nat Prod. 2012 Dec 28;75(12):2223-7.

Five novel eudesmene-type sesquiterpenes, kandenols A-E (1-5), have been isolated from Streptomyces sp. HKI0595 derived from the mangrove plant Kandelia candel. Their structures were established through NMR and mass spectrometry, and absolute configurations were established by the Mosher method and comparison of CD spectra with alpha-rotunol and Beta-Rotunol. The kandenols are reminiscent of various plant-derived eudesmenes, yet kandenols B and C are unusual because of their hydroperoxide moieties. Kandenol E is the first bacterial agarofuran, which belongs to an important group of antibiotics. Whereas the kandenols display no cytotoxicity against 12 human cell lines, weak to moderate antimicrobial activities were detected against Bacillus subtilis ATCC 6633 and Mycobacterium vaccae IMET 10670.

Synthesis of Spirovetivane Sesquiterpenes from Santonin. Synthesis of (+)-Anhydro-beta-rotunol and all diastereomers of 6,11-spirovetivadiene.[Pubmed:15471483]

J Org Chem. 2004 Oct 15;69(21):7294-302.

The synthesis of the spirovetivane sesquiterpenes (+)-anhydro-Beta-Rotunol and all the diastereomers of 6,11-spirovetivadiene in enantiomerically pure form has been achieved starting from santonin. The key step is the silicon-guided acid-promoted rearrangement of a 1-trimethylsilyl-4,5-epoxyeudesmane prepared from santonin in several steps involving lactone reductive opening, conjugate addition of TMSLi-CuCN, deoxygenation of a carbonyl group, and epoxidation. Rearrangement of the epoxide gave a spiro[4,5]decanediol which was used as a synthetic intermediate. From this compound, (+)-anhydro-Beta-Rotunol was prepared after elimination of the primary hydroxyl group in the side chain, followed by allylic oxidation at C8 and elimination of the tertiary hydroxyl group in the cyclohexane ring. On the other hand, elimination of the hydroxyl group in the side chain and reduction of the hydroxyl in the cyclohexane ring gave (-)-premnaspirodiene and (-)-hinesene. The synthesis of the rest of the diastereomers for these compounds required formal inversion of the C5 spiro carbon. The synthesis of these compounds showed that the structure of (-)-agarospirene isolated from Scapania sp. was erroneously assigned, and it has been corrected to be identical to that of (-)-hinesene.

Sesquiterpenoids from the roots of Solanum aethiopicum.[Pubmed:11371006]

Z Naturforsch C. 2001 Mar-Apr;56(3-4):181-7.

Three new sesquiterpenoids, lubiminoic acid, epilubiminoic acid and aethione, and six known sesquiterpenoids, solavetivone, 3beta-hydroxysolavetivone, 13-hydroxysolavetivone, anhydro-Beta-Rotunol, epilubimin and lubimin, were isolated from roots of S. aethiopicum L. Their structures were elucidated by spectroscopic data.

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