Grape Seed Extract is a natural product isolated from whole grape seeds that have a great concentration of vitamin E, flavonoids, linoleic acid, and OPCs. It has a number of health advantages, including an anti-inflammatory effect. The fat-metabolizing enzymes lipoprotein lipase and pancreatic lipase are inhibited by grape seed extract.
Physicochemical Properties
| Molecular Formula | C₃₀H₁₂O₆ | |
| Molecular Weight | 468.42 | |
| Exact Mass | 590.178 | |
| CAS # | 84929-27-1 | |
| Related CAS # |
|
|
| PubChem CID | 78577443 | |
| Appearance | Brown to reddish brown solid | |
| LogP | 3.3 | |
| Hydrogen Bond Donor Count | 9 | |
| Hydrogen Bond Acceptor Count | 11 | |
| Rotatable Bond Count | 3 | |
| Heavy Atom Count | 43 | |
| Complexity | 970 | |
| Defined Atom Stereocenter Count | 5 | |
| SMILES | CC1=CC(=C(C2=C1C[C@@]([C@H](O2)C3=CC(=C(C=C3)O)O)(C)O)[C@H]4[C@@H]([C@H](OC5=CC(=CC(=C45)O)O)C6=CC(=C(C=C6)O)O)O)O |
|
| InChi Key | VWKAFYWVDIOMSL-PMFFMQSYSA-N | |
| InChi Code | InChI=1S/C32H30O11/c1-13-7-22(38)26(30-17(13)12-32(2,41)31(43-30)15-4-6-19(35)21(37)9-15)27-25-23(39)10-16(33)11-24(25)42-29(28(27)40)14-3-5-18(34)20(36)8-14/h3-11,27-29,31,33-41H,12H2,1-2H3/t27-,28-,29+,31+,32+/m0/s1 | |
| Chemical Name | (2R,3S,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-3,5-dimethyl-2,4-dihydrochromen-8-yl]-3,4-dihydro-2H-chromene-3,5,7-triol | |
| Synonyms |
|
|
| HS Tariff Code | 2934.99.9001 | |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
|
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro |
Grape seed extract (25-100 μg/mL; 12-48 hours) inhibits the growth of and causes the death of human colorectal cancer cells[3]. Grape seed extract (25-100 μg/mL; 12-24 hours) modulates the protein levels of molecules that control the cell cycle in HT29 and LoVo cells[3]. Grape seed extract (25-100 μg/mL; 24 hours) causes human colorectal cancer cells to undergo apoptotic cell death[3]. |
| ln Vivo |
Grape seed extract (200 mg/kg; i.g.; 5 days/wk; for 8 weeks) inhibits the growth of HT29 colon carcinoma tumor xenografts in athymic nude mice[3]. In tumors, grape seed extract decreases cell proliferation while increasing apoptotic cell death[3]. In tumors, grape seed extract increases poly(ADP-ribose) poly-merase cleavage and Cip1/p21 protein levels[3]. |
| Animal Protocol |
Athymic male nu/nu mice, with human colon carcinoma HT29 tumor xenograft[3] 200 mg/kg Oral gavage, 5 days/wk, for 8 weeks |
| References |
[1]. The effects of grape seed extract (Vitis vinifera) supplement on inflammatory markers, neuropeptide Y, anthropometric measures, and appetite in obese or overweight individuals: A randomized clinical trial. [2]. Inhibitory effects of grape seed extract on lipases. Nutrition. 2003 Oct;19(10):876-9. [3]. Grape seed extract inhibits in vitro and in vivo growth of human colorectal carcinoma cells. Clin Cancer Res. 2006 Oct 15;12(20 Pt 1):6194-202. |
| Additional Infomation | See also: Grape Seed Extract (annotation moved to). |
Solubility Data
| Solubility (In Vitro) |
|
|||
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 0.6 mg/mL (Infinity mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 6.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 0.6 mg/mL (Infinity mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 6.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.1348 mL | 10.6742 mL | 21.3484 mL | |
| 5 mM | 0.4270 mL | 2.1348 mL | 4.2697 mL | |
| 10 mM | 0.2135 mL | 1.0674 mL | 2.1348 mL |