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29-Hydroxyfriedelan-3-one

CAS# 39903-21-4

29-Hydroxyfriedelan-3-one

Catalog No. BCN5453----Order now to get a substantial discount!

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29-Hydroxyfriedelan-3-one: 5mg $811 In Stock
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Quality Control of 29-Hydroxyfriedelan-3-one

Number of papers citing our products

Chemical structure

29-Hydroxyfriedelan-3-one

3D structure

Chemical Properties of 29-Hydroxyfriedelan-3-one

Cas No. 39903-21-4 SDF Download SDF
PubChem ID 14108943 Appearance Powder
Formula C30H50O2 M.Wt 442.7
Type of Compound Triterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (4R,4aS,6aS,6aS,6bR,8aS,11R,12aR,14aS,14bS)-11-(hydroxymethyl)-4,4a,6a,6b,8a,11,14a-heptamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1H-picen-3-one
SMILES CC1C(=O)CCC2C1(CCC3C2(CCC4(C3(CCC5(C4CC(CC5)(C)CO)C)C)C)C)C
Standard InChIKey NAOCHKKFDYTOII-MGIZKUGISA-N
Standard InChI InChI=1S/C30H50O2/c1-20-21(32)8-9-22-27(20,4)11-10-23-28(22,5)15-17-30(7)24-18-25(2,19-31)12-13-26(24,3)14-16-29(23,30)6/h20,22-24,31H,8-19H2,1-7H3/t20-,22+,23-,24+,25+,26+,27+,28-,29+,30-/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.

Source of 29-Hydroxyfriedelan-3-one

The herbs of Euonymus alatus (Thunb.) Sieb

Biological Activity of 29-Hydroxyfriedelan-3-one

In vitro

Isolation and frontier molecular orbital investigation of bioactive quinone-methide triterpenoids from the bark of Salacia petenensis.[Pubmed: 11270725]

Planta Med. 2001 Feb;67(1):65-9.


METHODS AND RESULTS:
The crude dichloromethane bark extract of Salacia petenensis (Hippocrateaceae) from Monteverde, Costa Rica, shows antibacterial and cytotoxic activity. Bioactivity-directed separation led to the isolation of tingenone and netzahualcoyonol as the biologically active materials. Also isolated from the extract were 3-methoxyfriedel-2-en-1-one (a new natural product) and 29-Hydroxyfriedelan-3-one. The structures of these compounds were elucidated on the basis of NMR spectral analysis. Molecular orbital calculations have been carried out using the semi-empirical PM3 and Hartee-Fock 3-21G ab initio techniques on the quinone-methide nortriterpenoids tingenone and netzahualcoyonol, as well as on the nucleotide bases adenine, guanine, cytosine, and thymine.
CONCLUSIONS:
The molecular orbital calculations suggest that a possible mode of cytotoxic action of quinone-methide triterpenoids involves quasi-intercalative interaction of the compounds with DNA followed by nucleophilic addition of the DNA base to carbon-6 of the triterpenoid.

Protocol of 29-Hydroxyfriedelan-3-one

Structure Identification
Phytochemistry,1984,23(3):631-3.

The chemistry of toxic principles from Maytenus nemerosa[Reference: WebLink]


METHODS AND RESULTS:
Maytenus nemerosa has been fractionated systematically by following the toxicity of extracts, partitioned solutions and column chromatographic fractions against cultured KB cells. Several compounds were isolated in this fashion, including 3-oxo-20(29)-lupen-30-al, β-amyrin, 29-Hydroxyfriedelan-3-one, 30-hydroxy-20(29)-lupen-3-one, 30-hydroxyfriedelan-3-one and lup-20(29)-ene-3β,30-diol, as well as tingenone, 20-hydroxytingenone and galactitol.
CONCLUSIONS:
3-Oxo-20(29)-lupen-30-al was shown to be cytotoxic for the first time; the structural basis of this cytotoxicity was investigated, in part, by bioassay of four products obtained by chemical transformation of single, isolated principles.

29-Hydroxyfriedelan-3-one Dilution Calculator

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Preparing Stock Solutions of 29-Hydroxyfriedelan-3-one

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.2589 mL 11.2943 mL 22.5887 mL 45.1773 mL 56.4717 mL
5 mM 0.4518 mL 2.2589 mL 4.5177 mL 9.0355 mL 11.2943 mL
10 mM 0.2259 mL 1.1294 mL 2.2589 mL 4.5177 mL 5.6472 mL
50 mM 0.0452 mL 0.2259 mL 0.4518 mL 0.9035 mL 1.1294 mL
100 mM 0.0226 mL 0.1129 mL 0.2259 mL 0.4518 mL 0.5647 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 29-Hydroxyfriedelan-3-one

Isolation and frontier molecular orbital investigation of bioactive quinone-methide triterpenoids from the bark of Salacia petenensis.[Pubmed:11270725]

Planta Med. 2001 Feb;67(1):65-9.

The crude dichloromethane bark extract of Salacia petenensis (Hippocrateaceae) from Monteverde, Costa Rica, shows antibacterial and cytotoxic activity. Bioactivity-directed separation led to the isolation of tingenone and netzahualcoyonol as the biologically active materials. Also isolated from the extract were 3-methoxyfriedel-2-en-1-one (a new natural product) and 29-Hydroxyfriedelan-3-one. The structures of these compounds were elucidated on the basis of NMR spectral analysis. Molecular orbital calculations have been carried out using the semi-empirical PM3 and Hartee-Fock 3-21G ab initio techniques on the quinone-methide nortriterpenoids tingenone and netzahualcoyonol, as well as on the nucleotide bases adenine, guanine, cytosine, and thymine. The molecular orbital calculations suggest that a possible mode of cytotoxic action of quinone-methide triterpenoids involves quasi-intercalative interaction of the compounds with DNA followed by nucleophilic addition of the DNA base to carbon-6 of the triterpenoid.

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