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Isovouacapenol C

CAS# 455255-15-9

Isovouacapenol C

2D Structure

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Isovouacapenol C

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Chemical Properties of Isovouacapenol C

Cas No. 455255-15-9 SDF Download SDF
PubChem ID 3009285 Appearance Powder
Formula C27H34O5 M.Wt 438.6
Type of Compound Diterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name [(4aR,5R,6R,6aS,7R,11aS,11bR)-4a,6-dihydroxy-4,4,7,11b-tetramethyl-2,3,5,6,6a,7,11,11a-octahydro-1H-naphtho[2,1-f][1]benzofuran-5-yl] benzoate
SMILES CC1C2C(CC3=C1C=CO3)C4(CCCC(C4(C(C2O)OC(=O)C5=CC=CC=C5)O)(C)C)C
Standard InChIKey YMUSGWGTHSRGHT-WVTZLOSNSA-N
Standard InChI InChI=1S/C27H34O5/c1-16-18-11-14-31-20(18)15-19-21(16)22(28)23(32-24(29)17-9-6-5-7-10-17)27(30)25(2,3)12-8-13-26(19,27)4/h5-7,9-11,14,16,19,21-23,28,30H,8,12-13,15H2,1-4H3/t16-,19-,21-,22+,23+,26+,27+/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 Isovouacapenol C

The roots of Caesalpinia pulcherrima

Biological Activity of Isovouacapenol C

DescriptionStandard reference

Protocol of Isovouacapenol C

Structure Identification
J Nat Prod. 2003 Oct;66(10):1378-81.

Cassane diterpenoids of Caesalpinia pulcherrima.[Pubmed: 14575441 ]


METHODS AND RESULTS:
Five new cassane diterpenoids (1-5) were isolated from the roots of Caesalpinia pulcherrima, along with the known Isovouacapenol C (6), pulcherrimin A (11), and 6beta-cinnamoyl-7beta-hydroxyvouacapen-5alpha-ol (12). Compounds 3-5 possess the alpha,beta-butenolide moiety, whereas compounds 1 and 2 contain a more usual 2,3-disubstituted furan unit. Compounds 7 and 8 were derived from hydrolysis of 6, while 9 and 10 were derived from acetylation and oxidation of 6, respectively.
CONCLUSIONS:
The (1)H and (13)C NMR spectra of all compounds were completely assigned using a combination of 2D NMR experiments, including (1)H-(1)H COSY, HSQC, HMBC, and T-ROESY sequences.

Acta Crystallogr Sect E Struct Rep Online. 2010 Jul 17;66(Pt 8):o2059-60.

Absolute configuration of isovouacapenol C.[Pubmed: 21588364 ]


METHODS AND RESULTS:
The title compound, C(27)H(34)O(5) {systematic name: (4aR,5R,6R,6aS,7R,11aS,11bR)-4a,6-dihy-droxy-4,4,7,11b-tetra-methyl-1,2,3,4,4a,5,6,6a,7,11,11a,11b-dodeca-hydro-phenanthro[3,2-b]furan-5-yl benzoate, Isovouacapenol C}, is a cassane furan-oditerpene, which was isolated from the roots of Caesalpinia pulcherrima. The three cyclo-hexane rings are trans fused: two of these are in chair conformations with the third in a twisted half-chair conformation, whereas the furan ring is almost planar (r.m.s. deviation = 0.003 Å). An intra-molecular C-H⋯O inter-action generates an S(6) ring. The absolute configurations of the stereogenic centres at positions 4a, 5, 6, 6a, 7, 11a and 11b are R, R, R, S, R, S and R, respectively.
CONCLUSIONS:
In the crystal, mol-ecules are linked into infinite chains along [010] by O-H⋯O hydrogen bonds. C⋯O [3.306 (2)-3.347 (2) Å] short contacts and C-H⋯π inter-actions also occur.

Isovouacapenol C Dilution Calculator

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Preparing Stock Solutions of Isovouacapenol C

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.28 mL 11.3999 mL 22.7998 mL 45.5996 mL 56.9995 mL
5 mM 0.456 mL 2.28 mL 4.56 mL 9.1199 mL 11.3999 mL
10 mM 0.228 mL 1.14 mL 2.28 mL 4.56 mL 5.7 mL
50 mM 0.0456 mL 0.228 mL 0.456 mL 0.912 mL 1.14 mL
100 mM 0.0228 mL 0.114 mL 0.228 mL 0.456 mL 0.57 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 Isovouacapenol C

Cassane diterpenoids of Caesalpinia pulcherrima.[Pubmed:14575441]

J Nat Prod. 2003 Oct;66(10):1378-81.

Five new cassane diterpenoids (1-5) were isolated from the roots of Caesalpinia pulcherrima, along with the known Isovouacapenol C (6), pulcherrimin A (11), and 6beta-cinnamoyl-7beta-hydroxyvouacapen-5alpha-ol (12). Compounds 3-5 possess the alpha,beta-butenolide moiety, whereas compounds 1 and 2 contain a more usual 2,3-disubstituted furan unit. Compounds 7 and 8 were derived from hydrolysis of 6, while 9 and 10 were derived from acetylation and oxidation of 6, respectively. The (1)H and (13)C NMR spectra of all compounds were completely assigned using a combination of 2D NMR experiments, including (1)H-(1)H COSY, HSQC, HMBC, and T-ROESY sequences.

Absolute configuration of isovouacapenol C.[Pubmed:21588364]

Acta Crystallogr Sect E Struct Rep Online. 2010 Jul 17;66(Pt 8):o2059-60.

The title compound, C(27)H(34)O(5) {systematic name: (4aR,5R,6R,6aS,7R,11aS,11bR)-4a,6-dihy-droxy-4,4,7,11b-tetra-methyl-1,2,3,4,4a,5, 6,6a,7,11,11a,11b-dodeca-hydro-phenanthro[3,2-b]furan-5-yl benzoate}, is a cassane furan-oditerpene, which was isolated from the roots of Caesalpinia pulcherrima. The three cyclo-hexane rings are trans fused: two of these are in chair conformations with the third in a twisted half-chair conformation, whereas the furan ring is almost planar (r.m.s. deviation = 0.003 A). An intra-molecular C-Hcdots, three dots, centeredO inter-action generates an S(6) ring. The absolute configurations of the stereogenic centres at positions 4a, 5, 6, 6a, 7, 11a and 11b are R, R, R, S, R, S and R, respectively. In the crystal, mol-ecules are linked into infinite chains along [010] by O-Hcdots, three dots, centeredO hydrogen bonds. Ccdots, three dots, centeredO [3.306 (2)-3.347 (2) A] short contacts and C-Hcdots, three dots, centeredpi inter-actions also occur.

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