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Hopane-3beta,22-diol

CAS# 22149-65-1

Hopane-3beta,22-diol

2D Structure

Catalog No. BCN4852----Order now to get a substantial discount!

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3D structure

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Hopane-3beta,22-diol

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Chemical Properties of Hopane-3beta,22-diol

Cas No. 22149-65-1 SDF Download SDF
PubChem ID 101277263 Appearance Powder
Formula C30H52O2 M.Wt 444.7
Type of Compound Triterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (3S,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-9-ol
SMILES CC1(C2CCC3(C(C2(CCC1O)C)CCC4C3(CCC5C4(CCC5C(C)(C)O)C)C)C)C
Standard InChIKey FNUXMEOWJVTJJE-DTXRQUTOSA-N
Standard InChI InChI=1S/C30H52O2/c1-25(2)21-13-18-30(8)23(28(21,6)16-14-24(25)31)10-9-22-27(5)15-11-19(26(3,4)32)20(27)12-17-29(22,30)7/h19-24,31-32H,9-18H2,1-8H3/t19-,20-,21-,22+,23+,24-,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 Hopane-3beta,22-diol

The herbs of Iodes cirrhosa

Biological Activity of Hopane-3beta,22-diol

DescriptionHopane-3beta,22-diol is a natural product from Iodes cirrhosa.

Protocol of Hopane-3beta,22-diol

Structure Identification
Eur J Biochem. 1980 Dec;112(3):541-7.

Non-specific biosynthesis of hopane triterpenes by a cell-free system from Acetobacter pasteurianum.[Pubmed: 7460938]


METHODS AND RESULTS:
The same cell-free system transformed (RS)-2,3-epoxy-2,3-dihydro-[12,13-3H]squalene into labelled 3 alpha-hydroxyhop-22(29)-ene, 3 beta-hydroxyhop-22(29)-ene, hopane-3 alpha,22-diol and Hopane-3beta,22-diol. Their radioactivity was similarly confirmed.
CONCLUSIONS:
This bacterial homogenate is thus capable of cyclizing an unnatural substrate, 2,3-epoxy-squalene, into 3-hydroxyhopanoids normally absent in the bacterium.

Hopane-3beta,22-diol Dilution Calculator

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Preparing Stock Solutions of Hopane-3beta,22-diol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.2487 mL 11.2435 mL 22.4871 mL 44.9741 mL 56.2177 mL
5 mM 0.4497 mL 2.2487 mL 4.4974 mL 8.9948 mL 11.2435 mL
10 mM 0.2249 mL 1.1244 mL 2.2487 mL 4.4974 mL 5.6218 mL
50 mM 0.045 mL 0.2249 mL 0.4497 mL 0.8995 mL 1.1244 mL
100 mM 0.0225 mL 0.1124 mL 0.2249 mL 0.4497 mL 0.5622 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 Hopane-3beta,22-diol

Non-specific biosynthesis of hopane triterpenes by a cell-free system from Acetobacter pasteurianum.[Pubmed:7460938]

Eur J Biochem. 1980 Dec;112(3):541-7.

1. A cell-free system from the bacterium Acetobacter pasteurianum was incubated with [12-3H]squalene; diploptene and diplopterol, hopanoids normally present in the bacterium, were labelled. Their radioactivity was confirmed by purification using thin-layer chromatography, synthesis of derivatives and recrystallization to constant specific activity. This demonstrates the direct cyclization of squalene into diploptene and diplopterol, catalysed by a squalene cyclase activity in A. pasteurianum. 2. The same cell-free system transformed (RS)-2,3-epoxy-2,3-dihydro-[12,13-3H]squalene into labelled 3 alpha-hydroxyhop-22(29)-ene, 3 beta-hydroxyhop-22(29)-ene, hopane-3 alpha,22-diol and hopane-3 beta,22-diol. Their radioactivity was similarly confirmed. This bacterial homogenate is thus capable of cyclizing an unnatural substrate, 2,3-epoxy-squalene, into 3-hydroxyhopanoids normally absent in the bacterium. 3. The 3 alpha-hydroxy and 3 beta-hydroxyhopanoids could have been enzymatically interconverted via the 3-oxo compound. Synthetic racemic (RS)-2,3-epoxy-2,3-dihydro-[3-3H]squalene was incubated and gave rise to 3-3H-labelled 3 alpha and 3 beta-hydroxyhopanoids. This excludes an isomerization via a 3-oxo compound which would give unlabelled 3-hydroxyhopanoids. 4. In conclusion, the cyclase of A. pasteurianum accepts the replacement of the normal substrate, squalene, by the corresponding epoxide. Furthermore it is not selective in the stereochemistry of the epoxide and cyclizes both enantiomers, contrary to the epoxysqualene cyclase of eukaryotes.

Description

Hopane-3β,22-diol (compound 74) is a hopane isolated from A. mariesii.

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