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Hydroxytyrosol

Hydroxytyrosol  Structure
CAS No.
10597-60-1
Chemical Name:
Hydroxytyrosol
Synonyms
4-(2-hydroxyethyl)benzene-1,2-diol;3-HYDROXYTYROSOL;3,4-DIHYDROXYPHENETHYL ALCOHOL;3,4-DIHYDROXYPHENYLETHYL ALCOHOL;Dopet;Dopaol;Dihydroxyphenylethanol;2-(3,4-DIHYDROXYPHENYL)ETHANOL;(S)-2-amino-3-(4-hydroxyphenyl)propane-1,1-diol;BA2774
CBNumber:
CB6477710
Molecular Formula:
C8H10O3
Molecular Weight:
154.16
MOL File:
10597-60-1.mol
MSDS File:
SDS
Modify Date:
2024/7/15 13:07:15

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 (Slightly)
form Solid
pka 9.72±0.10(Predicted)
color Colourless to Yellow Sticky Oil
BRN 2208118
Stability Hygroscopic
InChI InChI=1S/C8H10O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,9-11H,3-4H2
InChIKey JUUBCHWRXWPFFH-UHFFFAOYSA-N
SMILES C1(O)=CC=C(CCO)C=C1O
LogP 0.020 (est)
CAS DataBase Reference 10597-60-1(CAS DataBase Reference)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P301+P312+P330
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26
WGK Germany  3
HS Code  29072990
NFPA 704
3
0 0

Hydroxytyrosol price More Price(7)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) H4291 3-Hydroxytyrosol ≥98% (HPLC) 10597-60-1 25MG ₹26477.95 2022-06-14 Buy
Sigma-Aldrich(India) H4291 3-Hydroxytyrosol ≥98% (HPLC) 10597-60-1 100MG ₹56668.88 2022-06-14 Buy
Sigma-Aldrich(India) 91404 3-Hydroxytyrosol analytical standard 10597-60-1 5MG ₹10153.85 2022-06-14 Buy
TCI Chemicals (India) D2756 3-Hydroxytyrosol min. 98.0 % 10597-60-1 1G ₹12800 2022-05-26 Buy
TCI Chemicals (India) D2756 3-Hydroxytyrosol min. 98.0 % 10597-60-1 5G ₹24500 2022-05-26 Buy
Product number Packaging Price Buy
H4291 25MG ₹26477.95 Buy
H4291 100MG ₹56668.88 Buy
91404 5MG ₹10153.85 Buy
D2756 1G ₹12800 Buy
D2756 5G ₹24500 Buy

Hydroxytyrosol Chemical Properties,Uses,Production

Chemical Properties

Brown oil is derived from Olea europaea leaves and is soluble in methanol, DMSO, and other solvents but insoluble in petroleum ether, ether, and chloroform. The molecular structure of hydroxytyrosol is created by replacing the hydrogen atom on the methyl group of ethanol with catechol. It possesses an alcohol hydroxyl group in the chain of ethanol with a benzene ring, along with phenolic hydroxyl groups like other phenolic substances. Its antioxidant activity is closely linked to its structure.

Characteristics

Hydroxytyrosol displays much more effective antioxidant characteristics, such as the scavenging of free radicals, breaking peroxidative chain reactions, preventing lipid peroxidation, inhibiting hypochlorous acid derived radicals, and so on, compared with other phenolic compounds in olive oil. It could be used in the dermocosmetic industry for the creation of products for protecting the skin from oxidative stress or used as a preservative in the food technology.

Definition

ChEBI: Hydroxytyrosol is a member of the class of catechols that is benzene-1,2-diol substituted by a 2-hydroxyethyl group at position 4. Isolated from Olea europaea, it exhibits antioxidant and antineoplastic activities. It has a role as a metabolite, an antioxidant and an antineoplastic agent. It is a member of catechols and a primary alcohol. It derives from a 2-(4-hydroxyphenyl)ethanol.

General Description

Hydroxytyrosol, found in olives, is a potent antioxidant in our bodies. It is considered one of the most powerful antioxidants, with an oxygen radical absorption capacity of about 4,500,000 μmolTE/100g. This is 10 times greater than green tea and more than double the antioxidant capacity of CoQ10 and oak extract. Hydroxytyrosol is used in cardiovascular drugs, and has miraculous effects on the prevention and treatment of arteriosclerosis, hypertension, heart disease, cerebral hemorrhage, etc., and is superior to similar drugs. It can also Inhibits the proliferation rate of cancer cells and induces apoptosis of cancer cells.

Biological Activity

Hydroxytyrosol is a phenolic component of olive oil that inhibits both 12- and 5-LO. The IC50 values for the inhibition of rat platelet 12-LO and rat neutrophil 5-LO are 4.2 and 13 μM, respectively. It does not inhibit, and may actually enhance, COX activity. Hydroxytyrosol also protects LDL from both biological and chemical oxidation, suggesting a potential mechanism for the protective effects of olive oil against atherosclerosis.

Mechanism of action

Hydroxytyrosol (3,4-dihydroxyphenylethanol, HTyr), a phenolic alcohol, has been hypothesized to exert a wide range of biological effects, cardioprotective, anticancer, neuroprotective antimicrobial, beneficial endocrine, and other effects. Initially, the wide variety of HTyr biological activities was associated with its potent antioxidant activity. HTyr acts as a free radical scavenger and metal chelator. The high antioxidant efficiency of HTyr is attributed to the presence of the o-dihydroxyphenyl moiety. It mainly acts as a chain breaker by donating a hydrogen atom to peroxyl-radicals (ROO*). In this way, fairly reactive ROO* is replaced with HTyr* radical, unreactive due to intramolecular hydrogen bonds in the phenoxy radical. However, it has been proposed that HTyr may confer additional antioxidant protection by increasing the endogenous defense systems against oxidative stress by activating different cellular signaling pathways. One proposed mechanism involves the HTyr-mediated induction of phase II detoxifying enzymes via nuclear factor E2-related factor 2 (Nrf2) activation in different tissues.

Side effects

Hydroxytyrosol (HTyr) is a phenolic alcohol considered by the nutraceutical and food industries to be an excellent food supplement with no known adverse effects.The no observed adverse effect level for HTyr is 50 mg/kg body weight per day. The EFSA Panel on Nutritional Products, Nutrition and Allergies (NDA) on the safety of hydroxytyrosol as a novel food concluded that the MoE at the intended use and use level is adequate for the target population. The Panel concluded that the novel food hydroxytyrosol was safe at the proposed use and use levels.

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