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Hydroxytyrosol CAS 10597-60-1

Molecular Formula: C8H10O3

Formula Weight: 154.16

ZSpharmac: Hydroxytyrosol Supplement

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Product Name: Hydroxytyrosol
CAS No: 10597-60-1
Purity: 99%

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Basic Info

Product Name:Hydroxytyrosol
Other Names:3,4-Dihydroxyphenylethanol
CAS:10597-60-1
Place of Origin:Shandong, China
Brand Name:ZSpharmac
Type:Plant Extracts
Appearance:Colourless to Yellow Sticky Oil to Solid
EINECS No.:600-704-3
Storage:-20°C
Provide:Hydroxytyrosol MSDS;
Hydroxytyrosol COA

What is Hydroxytyrosol?

Hydroxytyrosol, an active ingredient in olives, acts as a highly active antioxidant in the human body. Antioxidants are bioactive molecules that are found in many plants, but their activity varies. Hydroxytyrosol is regarded as one of the most powerful antioxidants and the market demand is increasing day by day. Its oxygen radical absorption capacity is about 4,500,000 μmol TE/100g: 10 times that of green tea, and more than 2 times that of CoQ10 and quercetin.

Professor Liu Jiankang, director of the Institute of Mitochondrial Biomedicine, Academy of Sciences of Xi’an Jiaotong University, cooperated with DSM Nutritional Products, Switzerland to systematically study the effect of hydroxytyrosol, a polyphenol extract in olive oil, from the perspective of molecular biology. , Studies have shown that this substance promotes mitochondrial function by promoting mitochondrial synthesis. They found that olive oil extract hydroxytyrosol (hydroxytyrosol) can effectively protect the oxidative damage and mitochondrial dysfunction of retinal pigment epithelial cells caused by acrolein, a toxic component of cigarettes. , the main mechanism of which is that hydroxytyrosol can induce a two-phase enzyme system with detoxification in cells. These results suggest that hydroxytyrosol may have a protective effect on smoking-induced retinal pigment epithelium degeneration, such as macular degeneration.

Hydroxytyrosol Properties:

Boiling point 355.4±27.0 °C(Predicted)
density 1.321±0.06 g/cm3(Predicted)
refractive index 1.5810-1.5860
storage temp. -20°C
solubility Acetonitrile (Slightly), DMSO (Slightly), Ethyl Acetate (Sparingly), Methanol (S
pka9.72±0.10(Predicted)
form Solid
color Colourless to Yellow Sticky Oil to

 

Hydroxytyrosol Uses

  1. Hydroxytyrosol has anti-inflammatory, vasodilatory and antibacterial effects, can avoid atherosclerosis, as well as can decrease the occurrence of certain cancers cells (such as bust, prostate, endometrium, digestive tract); Antioxidant task and also the effect of decreasing the occurrence of cancer cells, for that reason have great assurance of medical impact.
  2. Hydroxytyrosol, a tyrosol metabolite, is also found in olive oil to have solid antioxidant properties.
  3. 1. Hydroxytyrosol is utilized in cardiovascular medications, as well as has incredible effects on the avoidance as well as treatment of arteriosclerosis, hypertension, cardiovascular disease, cerebral hemorrhage, and so on, and also transcends to comparable drugs.
    2. As a safe and also efficient anti-oxidant, hydroxytyrosol is made use of in elegance items as well as healthcare products, which can effectively boost skin flexibility and hydrating, and also has the result of wrinkle removal as well as anti-aging.
    3. The application of hydroxytyrosol in anti-cancer as well as anti-cancer: can avoid and deal with lung cancer, breast cancer cells, uterus.
    Hydroxytyrosol is a metabolite of oleuropein. Anti-oxidants. Inhibits the spreading rate of cancer cells as well as generates apoptosis of cancer cells.

Preparation of Hydroxytyrosol

method one:

A kind of preparation of hydroxytyrosol and a method for rapid nitration thereof:

(1) Extraction-extraction in parallel: Weigh a certain amount of olive pomace powder dried in the sun, use a mixed biphasic solvent that integrates extraction-extraction, and the ratio of olive pomace to solvent is 1:10~50 (w /v), the extraction temperature is about 20-25°C at room temperature, the extraction time is 1~60min, and the ultrasonic power is 100~1100W, carry out ultrasonic extraction-extraction, and then use a separating funnel to collect the upper layer of the solution, namely ethyl acetate Floor. The above-mentioned biphasic polar solvent is a mixed solution of ethanol-water-ethyl acetate.

(2) Column separation: Concentrate the collected solution of (1) by rotary evaporation at 25-50°C and 150 rpm to obtain a certain amount of concentrated solution, which is separated by silica gel resin, first adsorbed for 5-10 min, and mixed with an appropriate proportion of polar The solvent is eluted, and 6-8 column volumes of the target collection solution are collected.

(3) Rotary evaporation: the target collected liquid is rotary evaporated to dryness at 25-50 °C, wherein the content of hydroxytyrosol can reach more than 90%.

(4) Nitration: The collected and concentrated hydroxytyrosol is mixed with NaNO2 dissolved by weak acid, and at room temperature, under the action of microwave, the reaction is carried out for 1-8 minutes for rapid nitration to synthesize 4-nitrohydroxytyrosol .

In the present invention, the reaction formula of 4-nitrohydroxytyrosol by rapid nitration of hydroxytyrosol is as follows:

(5) Drying: the reaction solution finally obtained in (4) was extracted with ethyl acetate, anhydrous Na SO was added to remove water, and the 4-nitro The yield of hydroxytyrosol can reach more than 90%, and the content can reach more than 95%.

The biphasic mixed solvent used in the extraction-extraction parallel described in the step (1) is an ethanol-water-ethyl acetate mixture, and the volume ratio thereof is 1:1:1-2:3:5.

In step (2), the polar mixed solvent is chloroform-methanol in a ratio of 9:1 to 1:1.

In the step (3), the rotary evaporation conditions are as follows: the temperature is 40~90° C., the vacuum degree is 0.06~0.09Mpa, and the rotating speed is 100~300rmp.

In step (4), the molar ratio of hydroxytyrosol and NaNO2 used in the nitration process is 1:2-2:1, the microwave power is 100-1000W, and the stirring speed is 100-500rpm.

In step (5), the number of times of ethyl acetate extraction is 3 to 5 times, 60 to 80 mL each time, and the vacuum drying conditions are: temperature 25-50° C., vacuum degree 0.06-0.1 Mpa, and time 12-18 h.

Method Two:

Weigh 2.5kg p-hydroxyphenethyl alcohol, dissolve in 100kg 0.1M pH=6.5 phosphate buffer, add 5kg ascorbic acid, add 1L of enzyme solution (specific activity 500U/mg), stir at 50°C for 60 minutes, and the reaction solution passes through Nanofiltration membrane, dialysate passed through styrene resin column (about 100kg resin), washed with water to effluent and detected no hydroxytyrosol spots with TLC, this washing solution was concentrated to 50kg, extracted 5 times with 100kg ethyl acetate, ethyl acetate The ester liquid was concentrated to recover the solvent to obtain 2.5 kg of pale yellow viscous matter with a hydroxytyrosol content of 88.3%.

Method three:

The purified polyphenol oxidase solution was embedded in chitosan and cross-linked with glutaraldehyde, and its activity was measured at 50U/mg; 5kg of p-hydroxyphenylethanol was dissolved in 2000L 0.05mol/L phosphate buffer (pH value 6.5), add 10kg ascaric acid, stir to dissolve, add 1kg of immobilized enzyme, stir and react at 50 ° C for 60 minutes, the obtained reaction also recovers the immobilized polyphenol oxidase by centrifugation, and the reaction solution is passed through the nanofiltration membrane, dialyzed. The liquid was passed through a styrene resin column (about 200kg resin), washed with water until the effluent was detected without hydroxytyrosol spots with TLC, this washing liquid was concentrated to 100kg, extracted 5 times with 100kg ethyl acetate, and the ethyl acetate liquid was concentrated to reclaim the solvent , to obtain 4kg of pale yellow viscous matter with a hydroxytyrosol content of 91.2%.

A Survey of Research on Hydroxytyrosol Activity

Hydroxytyrosol has been shown to have various in vitro antioxidant activities, which can scavenge hydrogen peroxide, hydroxyl and other free radicals as well as reactive nitrogen free radicals and superoxide anions. And block the peroxidation chain reaction, inhibit the generation of metal ion catalyzed products of ROS, etc.

There are several reports that hydroxytyrosol has DPPH scavenging activity. These studies point to the EC of hydroxytyrosol. . The value is 20.5 anal mol/I. and 19 Hong mol/L, the EC of oleuropein. . The values ​​were 25.2 anal mol/I. and 22/,mol/L. Briante et al. obtained a series of hydrolyzed products such as oleuropein aglycone, hydroxytyrosol and olive acid after hydrolyzing oleuropein by extreme thermophilic p-glycosidase, and studied their activity in inhibiting the rate of fatty acid peroxidation. Both oleuropein and hydroxytyrosol were found to have stronger antioxidant capacity than olive acid.

In addition, some researchers have studied the antioxidant activity of hydroxytyrosol in humans. It is shown that the hydroxytyrosol-rich extract obtained from the wastewater of olive oil processing plants can effectively prevent the oxidation of human LDL (inducing the pathogenesis of atherosclerosis) and remove superoxide anions and Hypochlorous acid.

Other researchers obtained an extract rich in hydroxytyrosol from olive leaves (hydroxytyrosol accounted for about 92% of the total phenols in the extract), and investigated its antioxidant activity. Results The extract showed good anti-oxidation effect of various food oils at a concentration of 100 mg/kg, and had no cytotoxicity and inhibited the growth of lactic acid bacteria, so it could be used as a food ingredient.

Hydroxytyrosol can inhibit or slow down the growth of a variety of human bacteria, fungi and pathogenic bacteria. Medina et al\’s study showed that hydroxytyrosol has strong broad-spectrum antibacterial activity, especially against Gram-positive bacteria. In addition, it is not only detrimental to harmful bacteria (C. perfringens, Escherichia coli) in the small intestinal flora, but also to beneficial bacteria, such as: Lactobacillus acidophilus and Bifidobacterium bifidum. Likewise, a variety of food-borne pathogens, such as Listeria monocytogenes, Staphylococcus aureus, Salmonella, and Shigella, were killed after 1 h of exposure to hydroxytyrosol.

Bisignano et al. also found that hydroxytyrosol has activity against a variety of human intestinal and respiratory pathogens. Recently, Brenes et al. also found that hydroxytyrosol has strong in vitro anti-Helicobacter pylori activity, indicating that it is promising as a preventive drug for peptic ulcer and gastric cancer. Through research, it is found that hydroxytyrosol mainly penetrates the bacterial cell mucosa, decomposes bacterial mucopeptides, or causes the damage of bacterial mucosa. The antibacterial activity of hydroxytyrosol is significantly better than that of oleuropein, which may be due to the glycoside structure of oleuropein, which makes it difficult to penetrate bacterial mucosa.

In addition to its antibacterial activity, oleuropein also has activity against a variety of fungi such as Fusarium elderberry, Verticillium dahliae, and tomato early blight. Gong et al. used 20% hydroxytyrosol orally to treat carrageenan-induced acute inflammation rats to evaluate the inhibitory effect of 20% hydroxytyrosol on toe swelling and pain in acutely inflammatory rats.

Determination of tumor necrosis factor-d (TNF-a), interleukin-1 (IL-lfl) and interleukin-10 (IL-10) in tissues by measuring reverse transcriptase polymerase chain reaction (RT-PCR) content level. The results showed that 20% hydroxytyrosol could effectively reduce the levels of pro-inflammatory cytokines IL-1 and TNF-α in tissues, but did not increase the mRNA expression of anti-inflammatory cytokines IL-10.

In addition to inhibiting LDL oxidation, studies have confirmed that hydroxytyrosol also inhibits platelet aggregation in vitro m 2I. Gonzfilez-Santiago et al. used the diet supplemented with hydroxytyrosol to feed hyperlipidemia rabbits, and the results confirmed that it effectively improved the body’s antioxidant capacity and weakened the degree of atherosclerotic lesions. Gonzfilez-Correa et al. investigated the anticoagulant effect of hydroxytyrosol on rat blood in vitro with acetylsalicylic acid as a control. The results showed that it could inhibit platelet aggregation and the synthesis of thromboxane B, and at the same time increase the production of NO, so as to achieve Anticoagulation. The anti-cardiovascular effects of hydroxytyrosol may be related to the reduction of blood glucose and lipid oxide concentrations.

Experiments have shown that hydroxytyrosol can reduce the blood glucose concentration in plasma and the amount of triacylglycerol and total cholesterol in serum of diabetic rats, and can enhance SOD, catalase (CAT) and glutathione (GSH) in liver and kidney. Peroxidase activity, reducing the content of alkaline phosphatase and thiobarbituric acid reactants, thus showing the effect of reducing liver and kidney organ toxicity, the mechanism may be related to the binding of hydroxytyrosol and LDL. There are also data that hydroxytyrosol can treat hyperglycemia and oxidative stress conditions caused by diabetes.

Hydroxytyrosol can also prevent the occurrence of atherosclerosis. Zrelli et al demonstrated that hydroxytyrosol can reduce the level of hydrogen peroxide-induced ROS in porcine pulmonary artery epithelial cells, and enhance mRNA enzyme, protein activity and the level of intracellular transcriptional regulator 3a (FOX03a), induce adenosine phosphate-activated protein kinase Translocates FOX03a to the nucleus. Among them, FOX03a is a transcriptional regulator that mainly exists in cardiac tissue. Its activation state has obvious effects on inhibiting the proliferation of vascular smooth muscle, cardiomyocyte hypertrophy and anti-oxidative stress, but it is inactivated when it is transported from the nucleus to the cytoplasm.

Hydroxytyrosol can protect epithelial cells from oxidative damage and prevent the occurrence of arteriosclerosis by inducing the expression of adenylate-activated protein kinase and activating the activity of FOX03a. In addition, hydroxytyrosol is also a powerful anti-oxidant in the brain. Experiments have shown that it can reduce the level of lipid peroxide products in the striatum and the rest of the brain, hinder the consumption of GSH, and ingest food containing hydroxytyrosol can reduce cranial nerves. risk of disease. The above studies all show that hydroxytyrosol can reduce the amount of reactive oxygen species in the brain and vascular endothelial cells, which provides a molecular basis for the treatment of cardiovascular and cerebrovascular diseases.

Research data show that hydroxytyrosol can inhibit multiple stages of tumorigenesis and has a broad spectrum. It is generally believed that tumors are caused by abnormal gene expression caused by excess free radicals and reactive oxygen species (ROS) in the body that damage DNA. Hydroxytyrosol has higher antioxidant activity and free radical scavenging ability than some other synthetic and natural compounds, and can effectively scavenge endogenous and exogenous free radicals and reactive oxygen species, thereby preventing the occurrence of cancer.

The relationship between chronic inflammation and tumorigenesis has attracted more and more attention, and some researchers believe that 15% to 20% of all cancers may originate from inflammatory infections. Thus, the cardioprotective anti-inflammatory activity of hydroxytyrosol suggests its potential anticancer activity. Hydroxytyrosol inhibits cyclooxygenase-2 (COX-2) and 5-lipoxygenase, and reduces the synthesis of prostaglandin E2, thereby inhibiting the occurrence of diseases such as cancer.

In addition, hydroxytyrosol can alter tumor eicosanoid biosynthesis, thereby exhibiting broad-spectrum anticancer activity, inhibiting proliferation and promoting apoptosis of human tumor cell lines through multiple mechanisms.

Company Profile and Corporate Culture

Company Profile:

ZhiShang Chemical is owned by ZhiShang Group is a professional new-type chemicals enterprise combined into research and development, production and sales .

The company’s competitive product is pharmaceutical raw materials and intermediates (especially carbohydrate derivatives Series), In recent years, the company has made a major breakthrough in food and feed additives, plant extraction, industrial chemicals industry .

The company insists on the spirit of “sincere management, strict quality control, customer as god” , get consistent high praise from customers at home and abroad.

Corporate Culture:

OUR MISSION
Help China Chemicals to benefit the happiness of human life
OUR VISSION
Become the most trusted chemical supplier in the world
OUR BUSINESS PHILOSOPHY
Striver – oriented, enrich employees, customer first, deep service, seek development
OUR VALUES
Be prepared for danger in times of peace, forge ahead actively, unity and cooperation, and be brave to fight

About Us

The production base is located in Zhangqiu chemical industry park and Tai’an high-tech chemical industry park. laboratory and workshop in strict accordance with the GMP standard and the product fit national ISO9001 and ISO2000 standards.

“Zhishang” products are exported to Europe, North and South America, the Middle East, Asia Pacific and Africa area, so as to establish a long-term and stable cooperation relationship with customer in the world.

Company Info
  • Business Type: Manufacturer
  • Product Range: Additive , Chemical Auxiliary & Catalyst , Organic Chemicals
  • Products/Service: Organic Intermediate,Inorganic Chemistry, APIs, Dyestuffs And Pigments, Fragrance And Spices, Food Additives
  • Total Employees: 51~100
  • Capital (Million US $): 10000000RMB
  • Year Established: 2016
Production Capacity
  • No. of Production Lines : 8
  • No. of QC Staff : 5 -10 People
  • OEM Services Provided : yes
  • Factory Size (Sq.meters) : 3,000-5,000 square meters
  • Certificate: ISO9001 , CE , GMP , API , MSDS
  • Factory Location : Diao Town Industry Park, Zhangqiu City, Jinan City, Shandong Province, China.

Service

Pre-Sales Service

* Prompt reply and 24 hours online, professional team to provide best price and high quality product.

* Sample testing support.

* Every batch of products will be tested to ensureits quality.

*The packing also can be according the customers` requirment.

*Any inquiries will be replied within 24 hours.

*we provide Commerical Invoice, Packing List, Bill of loading, COA , Health certificate and Origin certificate. If your markets have any special requirements, let us know.

 

After-Sales Service

*The fact of logistics information monitoring.

* Any questions about the product can be consulted at any time.

*Product has any problem can return.

FAQ

Do you accept sample order?

We will make samples before mass production, and after sample approved, we’ll begin mass production. Doing 100% inspection during production, then do random inspection before packing.

 

HOW TO CONFIRM THE PRODUCT QUALITY BEFORE PLACING ORDERS?

You can get free samples for some products,you only need to pay the shipping cost or arrange a courier to us and take the samples. You can send us your product specifications and requests,we will manufacture the products according to your requests.

What’s your MOQ?

Our MOQ is 1kg. But usually we accept less quantity such as 100g on the condition that sample charge is 100% paid.

Do you supply product report?

Yes. We’ll give you product analysis report before shipping.

  Is there a discount?

Different quantity has different discount.

Shipping

1. ≤50kg, Express delivery recommended, usually called as DDU service;

2. ≤500kg, Air shipping recommended, usually called as FOB, CFR, or CIF service;

3. >500kg, sea shipping recommended, usually called as FOB, CFR, or CIF service;

4. For high value products, please select air shipping and express delivery for safe.

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