Grape Seed Extract Chemical Properties

Density 

0.961g/cm3 at 20℃

vapor pressure 

0.003Pa at 60℃

FEMA 

4045 | GRAPE SEED EXTRACT

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Soluble in DMSO

form 

Solid:particulate/powder

color 

Brown to reddish brown

InChIKey

VWKAFYWVDIOMSL-PSXRJWADNA-N

SMILES

[C@H]1(C2=CC=C(O)C(O)=C2)OC2=C(C(O)=CC(O)=C2)[C@@H](C2C3O[C@H](C4=CC=C(O)C(O)=C4)[C@@](O)(C)CC=3C(C)=CC=2O)[C@@H]1O |&1:0,18,22,31,41,r|

LogP

6.5 at 25℃ and pH5-6

Grape Seed Extract Usage And Synthesis

Medicinal value of grape seed

Grape seed have good effects on benefit “qi” and blood, strengthen the bones, diuresis, treatment of weak “qi” and blood, lung deficiency and cough, night sweats, palpitations, rheumatism, gonorrhea, and edema, etc. Modern research shows that the original anthocyanin of the grape seed extract has effects on anti-oxidation and reducing cholesterol level, making it a potential natural antioxidant. Therefore, it can be used for prevention and treatment of high cholesterol level, atherosclerosis, cataracts, stomach ulcers, intestinal adenocarcinoma, Ehrlich ascites carcinoma, etc. Its main pharmacological effects are as follows:
1. antioxidant: polyphenols of grape seed extract including proanthocyanidins and the phenolic hydroxyl of gallic acids provide specific hydrogen atoms so that they have a strong antioxidant effect. Its ability of neutralizing and attacking the Iron and oxygen in lipids is 15 to 25 times of the VB. Moreover, it has a stronger effect on scavenging free radical than VC.VE and other antioxidants.
2. anti-radiation effects: inhibit the lipid peroxidation caused by radiation.
3. anti-inflammatory effect: its main component is proanthocyanidins, whose anti-oxidation effect can inhibit the synthesis and release of histamine, serotonin, prostaglandins and leukotrienes and other inflammatory cytokines. It also inhibits the basophils and mast cells to release particles, inhibits the activity of histamine decarboxylase, and limiting the role of hyaluronidase.
4. Prevention of cataracts: Catechins is the main component for cataract prevention; grape seed extract can strengthen the myopic retinal and improve the insight of patients in a non-inflammatory form. It can also relieve the eye fatigue.
5. Anti-cancer effect: It has cytotoxicity to the MCF-7 human breast tumor cells, A-427 human lung cancer cells and human gastric adenocarcinoma cells CRL1739. It also prevents the carcinogenesis effect of intestinal chemical carcinogens.
6. Anti-atherosclerotic effect: Food containing 2.5% grape seed extract, can reduce the cholesterol ester peroxide levels in serum of experimental animal, also lower the LDL (low density lipoprotein) level against atherosclerosis. It can further improve blood rheology and platelet aggregation.
7. Cholesterol-lowering effect: Tannin gallic acid ester can reduce the levels of total plasma cholesterol, triglycerides esters, LDL cholesterol and very low density cholesterol, and increase HDL cholesterol levels.
8. Anti-ulcer effect: The oligomeric proanthocyanidins in grape seed extract can protect the gastric mucosa from damage. Proanthocyanidins can also scavenge the free radical on stomach surface and protect the gastric wall.
9. Anti-mutagenic effect: can reduce the incidence of mitochondria mutation and nuclear mutation.
The above information is edited by the Chemicalbook of Dai Xiongfeng.

Plant Extract

Grape seed extract is a plant extract, with the main ingredient, proanthocyanidins (cannot synthesized in vivo of human body), which is a novel natural anti-oxidant extracted from grape seeds. It is currently one of the most efficient plant-derived anti-oxidant. Both in vivo and in vitro tests showed that the antioxidant effect of grape seed extract is 50 times of vitamin E, 20 times stronger than vitamin C. It can effectively remove excess free radicals in the human body, thus having a superior anti-aging effect and can enhance immunity ability. The main known effects include anti-inflammatory, anti-histamine, anti-allergic, anti-allergen, anti-oxidation, anti-fatigue and improving physical fitness, improving the sub-health state and suppressing aging, treating irritability, alleviating dizziness, fatigue and hypomnesia, beauty, promoting blood circulation and so on.
In Europe, grape seed is known as "oral skin cosmetics." Grape seed is a natural sun shelter, which can keep the skin away from ultraviolet rays. The sun can kill 50% of human skin cells; but if be protected by grape seed, about 85% of the skin cells can finally survive. Owing to the special affinity of proanthocyanidins (OPC) in grape seed to the skin collagen and elastic fibers, it is possible to protect them from damage.
Grape seed extract is a main functional ingredient of cosmetics for oriental women. By inhibiting the activity of tyrosinase, it scavenges free radicals and reduces melanin deposition and skin inflammation occurrence. Thus it has the effect of convergence, tightening the skin and preventing skin wrinkle from appearing early. Long-term use can make the skin smooth and elastic with a effect of beauty.

Chemical Properties

Grape seed extract has an astrigent taste.

Occurrence

Grapeseed is found throughout the world.

Uses

Grapeseed may be used as an antioxidant and an anticancer treatment. It may also be used to treat varicose veins, circulatory problems, and vision problems such as cataracts, and to improve vision by lessening eye strain.

Uses

Grape seed extract is a natural product, with anti-inflammatory and anti-proliferative effects. Grape seed extract shows inhibitory activity on the fat-metabolizing enzymes pancreatic lipase and lipoprotein lipase. Grape seed extract induces apoptotic in human colorectal cancer cells.

Composition

Standardized grape seed extracts are reported to contain 74 to 78% oligomeric proanthocynidins and less than approx- imately 6% of free favanol monomers on a dry weight basis Specifcally, grape seed extract contains the favanol monomers (+)-cat- echin, (–)-epicatechin, (–)-epicatechin gallate, (–)-epigallocatechin and (–)-epigallocatechin gallate.

Anticancer Research

Grape seed extract (GSE) has high quantities of proanthocyanidins and resveratrol.Human colorectal cancer cell (CRC) exposure to GSE (Schonthal 2012) resulted inmodified ER chaperones glucose-related protein-78 (GRP78) and protein disulphideisomerase (PDI). GRP78 is needed for integrity of ER as well as stress-inducedautophagy (Flaumenhaft et al. 2015). PDI, a thiol-disulphide oxidoreductase,catalyses the disulphide bonds in newly synthesized proteins in the ER lumen (Hanet al. 2013; Wang and Kaufman 2014; Perri et al. 2016), and PDIA3 is localized tothe ER and is involved in protein folding (Wang et al. 2012b). Studies on the role ofPDI in cancer have demonstrated a pro-oncogenic, pro-survival role for PDI incancer and therapeutic resistance. PDI aids in ameliorating stress-induced apoptosisand causes degradation of wrongly folded proteins (Dinicola et al. 2010; Xu et al.2014). Hence, any obstruction caused in the activity of PDI will induce stress in thecell and lead to cell apoptosis. Fructose bisphosphate aldolase, a key enzymeinvolved in glycolysis, is also a potential target of GSE (Vandewynckel et al. 2016).The ER stress leads the cell to undergo apoptotic pathways in multiple ways andhence inhibits the proliferation of the targeted cells (Farooqi et al. 2015).

Safety

Grape seed extract is generally well tolerated when taken in moderate amounts. It has been tested safely for up to 11 months in human studies. It’s possibly unsafe if you have a bleeding disorder or are going to have surgery or if you take anticoagulants (blood thinners), such as warfarin or aspirin. Little is known about whether it’s safe to use grape seed extract during pregnancy or while breastfeeding.

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