3D Mol Similar

Resveratrol

: Iupac Name：5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol; CAS No.: 501-36-0; Molecular Weight：228.24; Modify Date.: 2022-11-06 07:41; Introduction: Resveratrol is a natural antioxidant. It can reduce blood viscosity, inhibit platelet aggregation and vasodilation, keep the blood flowing and prevent the occurrence and development of cancer. It has the function to prevent and treat atherosclerosis, coronary heart disease, ischemic heart disease and high blood cholesterol. It has an effect on suppressing tumor. Resveratrol also has estrogen-like effects that can be used to treat breast cancer and other diseases. It can retard aging and prevent cancer. Red grape skins, red wine and grape juice have high concentrations of resveratrol. Studies have shown that the integrity of the chromosomes will be destroyed as the human aging. But resveratrol can activate proteins that can repair chromosome, thus delaying aging.Resveratrol is a polyphenolic phytoalexin. It is also classified as a stilbenoid, a derivate of stilbene, and is produced in plants with the help of the enzyme stilbene synthase. The levels of resveratrol found in food varies greatly. Red wine contains between 0. 2 and 5. 8 mg/L depending on the grape variety, while white wine has much less. The reason for this difference is that red wine is fermented with grape skins, allowing the wine to absorb the resveratrol, whereas white wine is fermented after the skin has been removed.Resveratrol is a very effective anti-oxidant with 95% efficiency in preventing lipid peroxidation as compared with 37% for Vitamin C or 65% for Vitamin E. It has very strong peroxyl radical scavenging abilities, more than gallic and ellagic acids and epicatechins. Resveratrol has been shown to protect against UVB mediated skin damage in mice by boosting anti-oxidant defenses, and it has been shown to help alleviate skin wounds.Resveratrol is effective against photoaging due, in part, to its anti-oxidant properties, and is recommended for use in pre- or post-sun exposure products. Resveratrol can pass through the stratum corneum to be found in the dermis and epidermis. It has been shown to preserve dermal collagen, and may be effective in enhancing glycosaminoglycans, which enhance tissue hydration. It has been shown to stimulate skin’s cellular renewal, and help increase skin's thickness. And it has been shown to inhibit tyrosinase, which indicates its use for reducing hyperpigmentation. View more+

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1. Names and Identifiers

: 1.1 Name; Resveratrol; 1.2 Synonyms; (E)-2-(3,5-Dihydroxyphenyl)-1-(4-hydroxyphenyl)ethene (E)-3,4′,5-Trihydroxystilbene (E)-5-(p-Hydroxystyryl)resorcinol (E)-Resveratrol 1,3-Benzenediol, 5-[(1E)-2-(4-hydroxyphenyl)ethenyl]- 1,3-Benzenediol, 5-[2-(4-hydroxyphenyl)ethenyl]-, (E)- 3,4',5'-TRIHYDROXY-TRANS-STILBENE 3,4',5-TRIHYDROXY-TRANS-STILBENE 3,4′,5-Stilbenetriol 3,4′,5-Trihydroxystilbene 3,4′,5-Trihydroxy-trans-stilbene 5-[(1E)-2-(4-Hydroxyphenyl)ethenyl]-1,3-benzenediol Biofort CA 1201 Cuspidatin Melinjo Resveratrol 20 Polygonin Regu-Fade Resveratrol P 5 RESVERATROLE Resvida SRT 501 SRT 501M TRANS-1,2-(3,4',5-TRIHYDROXYDIPHENYL)ETHYLENE TRANS-3,4,5-TRIHYDROXYSTILBENE trans-3,5,4′-Trihydroxystilbene TRANS-3,5,4'-STILBENETRIOL TRANS-RESVERATROL Vineatrol 20M; View all

1.3 CAS No.: 501-36-0

1.4 CID: 445154

1.5 EINECS(EC#): 610-504-8

1.6 Molecular Formula: C14H12O3 (isomer)

1.7 Inchi: InChI=1S/C14H12O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h1-9,15-17H/b2-1+

1.8 InChIkey: LUKBXSAWLPMMSZ-OWOJBTEDSA-N

1.9 Canonical Smiles: C1=CC(=CC=C1C=CC2=CC(=CC(=C2)O)O)O

1.10 Isomers Smiles: C1=CC(=CC=C1/C=C/C2=CC(=CC(=C2)O)O)O

2. Properties

2.1 Density: 1.359

2.1 Melting point: 253-255°C

2.1 Boiling point: 449.1 oC at 760 mmHg

2.1 Refractive index: 1.763

2.1 Flash Point: 222.3 oC

2.1 PSA: 60.69000

2.1 logP: 2.97380

2.1 Appearance: Off-White to Tan Powder

2.2 Storage: Store at -20°C.

2.3 Chemical Properties: Off-White to Tan Powder

2.4 Color/Form: Off-white

2.5 Decomposition: When heated to decomposition it emits acrid smoke and irritating vapors.

2.6 pKa: 9.22±0.10(Predicted)

2.7 Water Solubility: Soluble in water (3 mg/100mL), ethanol (50 mg/mL), DMSO (16 mg/mL), DMF (~65 mg/mL), PBS (pH 7.2) (~100µg/mL), methanol, and acetone (50 mg/mL).

2.8 Spectral Properties: UV: 4-504 (Phillip et al., Organic Electronic Spectral Data, John Wiley & Sons, New York)

2.9 Stability: Stable at normal temperatures and pressures.

2.10 StorageTemp: ?20°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A resveratrol in which the double bond has E configuration.

3.2 Usage: Resveratrol can prevent the oxidation of low density lipoprotein, and has the potential effect on preventing cardiovascular disease, cancer, antivirus and immune regulation. Its main role is antioxidant properties.Cardiovascular drugs. It can reduce hematic fat and prevent heart disease. It also has the effect on AIDS.Antioxidants and the activity in anti-inflammatory, antithrombotic, anti-cancer, anti-cancer, anti hyperlipidemia and antibacterial.Anti-aging, regulating blood lipid, cardiovascular protection, anti-hepatitis.Resveratrol is a phytoalexin produced naturally by several plants with anti-cancer, anti-inflammatory, blood-sugar-lowering and other beneficial cardiovascular effects.

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: 37/38-41-36/38-36-43-22

4.1 Safety Statements: 26-39-37/39-36/37/39

4.1 Octanol/Water Partition Coefficient: log Kow = 3.08 (est)

4.2 DisposalMethods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

4.3 Formulations/Preparations: Supplied as capsules & tablets
Trade names: Protykin Resveratrol ... Resveratrol Antioxidant Protection ...
Resveratrol marketed as a nutritional supplements, is typically an extract of Polygonum cuspidatum ... Such an extract contains both cis- and trans-resveratrol. The extracts are usually standardized to deliver ca 8% resveratrol in its various forms. Many of the products currently marketed have resveratrol in combination with other phytonutrients and vitamins ...

4.4 WGK Germany: 3

4.4 RTECS: CZ8987000

4.4 Safety: Mutation data reported. When heated to decomposition, it emits acrid smoke and irritating vapors.
Hazard Codes:?Xi
Risk Statements: 37/38-41-36/38?
R37/38:Irritating to respiratory system and skin.?
R41:Risk of serious damage to the eyes.?
R36/38:Irritating to eyes and skin.
Safety Statements: 26-39-37/39?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S39:Wear eye / face protection.?
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 3
RTECS: CZ8987000

4.5 Specification: ?Resveratrol , its cas register number is 501-36-0. It also can be called 3,4',5-Trihydroxy-trans-stilbene ; and 5-[(1E)-2-(4-Hydroxyphenyl)ethenyl]-1,3-benzenediol .?Resveratrol (CAS NO.501-36-0) sholud be kept tightly closed or stored at correct temperature. Th first aid measures are as follow: When in the eyes, hold eyelids apart and flush eyes with plenty of water. After initial flushing, remove any contact lenses and continue flushing for at least 20 minutes. Have eyes examined and tested by medical personnel.?If it was?inhaled: Remove from exposure and move to fresh air immediately. Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And get medical aid immediately. If swallowed, wash out mouth with water provided person is conscious. Never give anything by mouth to an unconscious person. Get medical attention. Do not induce vomiting unless directed to do so by medical personnel.?

4.6 Toxicity

1.	???	dni-hmn-oth 30 μmol/L/24H	???	CALEDQ ?? Cancer Letters (Shannon, Ireland). 163 (2001),49.
2.	???	dni-hmn-leu 20 μmol/l/8H	???	CALEDQ ?? Cancer Letters (Shannon, Ireland). 140 (1999),1.
3.	???	sce-ham-lvr 10?mg/L/48H	???	MUREAV ?? Mutation Research. 494 (2001),107.
4.	???	cyt-ham-lvr 10?mg/L/48H	???	MUREAV ?? Mutation Research. 494 (2001),107.
5.	???	mnt-ham-lvr 10?mg/L/48H	???	MUREAV ?? Mutation Research. 494 (2001),107.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Eye irritation, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H319 Causes serious eye irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention.
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

7. Synthesis Route

501-36-0Total: 100 Synthesis Route

99-10-5 200 Suppliers

501-36-0 831 Suppliers

Literatures:
Andrus, Merritt B.; Liu, Jing; Meredith, Erik L.; Nartey, Edward Tetrahedron Letters, 2003 , vol. 44, # 26 p. 4819 - 4822
Yield: null

104-01-8 228 Suppliers

501-36-0 831 Suppliers

Literatures:
Davis, Matthew C.; Parrish, Damon A.; Harvey, Benjamin G. Organic Preparations and Procedures International, 2013 , vol. 45, # 4 p. 304 - 313
Yield: null

134-96-3 165 Suppliers

501-36-0 831 Suppliers

Literatures:
Davis, Matthew C.; Parrish, Damon A.; Harvey, Benjamin G. Organic Preparations and Procedures International, 2013 , vol. 45, # 4 p. 304 - 313
Yield: null

View all

8. Precursor and Product

precursor:

1132-21-4

100-66-3

836-43-1

501-36-0

2150-37-0

105-13-5

4397-53-9

99-10-5

6652-32-0

123-08-0

1145-93-3

156-38-7

104-01-8

134-96-3

2628-16-2

696-62-8

877-88-3

705-76-0

7311-34-4

123-11-5

5736-94-7

5544-60-5

540-38-5

824-94-2

108-73-6

View all

product :

501-36-0

4359-97-1

7311-34-4

858187-22-1

99-10-5

27208-80-6

123-08-0

5406-18-8

38963-95-0

4179-19-5

537-42-8

58436-29-6

411233-11-9

89946-04-3

42206-94-0

59623-12-0

View all

9. Other Information

9.0 Merck: 14,8158

9.1 resveratrol sources plants: Resveratrol is anthraquinone terpenoids. It mainly comes from rhizome extract of polygonum cuspidatum. Polygonum cuspidatum: Shrubby perennial herb, up to 1 meter or more. Rhizome lying underground, wood brown, section significantly. Stems erect and cylindrical, surface glabrous, scattered with most red spots, hollow. Leaves alternate, broadly ovate to nearly circular, long 7-12cm, width 5-9cm, apex mucronate, base rounded or cuneate; petiole 1-1.5cm sheath care quality, brown, early fall. Flowering is from July to September, and fruiting from September to October. Spring and autumn can be excavated, cut and dried. Polygonum cuspidatum is born in the valley, creek or shore.

9.2 Contents determination method: C18 column, mobile phase consisted of acetonitrile and water (volume ratio 30: 70), and UV detection at 30 6nm are used to detect. The results show that if the concentration of resveratrol is in 10~250 μg/mL, concentration and peak area show a good linear relationship (r = 0.9999); the recovery is 925% to 1026%; the lowest detectable concentration is 0.6mg/g. The flow rate can be adjusted to detect the enzymatic conversion of polydatin and resveratrol at the same time.

9.3 The synthetic method of resveratrol: Resveratrol is an inhibitor of many oxidative metabolism enzymes of aromatic carcinogens. It is named as the natural chemopreventive agents of cardiovascular and cerebrovascular diseases and cancer. Many studies have shown that resveratrol also has many functions, such as anti-mutagenic activity, protecting cell toxicity induced by the oxidation of lipoprotein, inhibiting tumor cell reproduction, and so on.
Human separated resveratrol from the root of veratrum grandiflorum for the first time in 1940. Researchers currently has found resveratrol from at least 21 families and 31 genera of 72 species of plants, such as grape vine genus, vitis snake, legumes arachis, cassia, sophora, polygonum, and so on. Because of the low concentration of resveratrol in the plant and the high extraction cost, using chemical, biological, genetic engineering and other methods to obtain resveratrol has become an indispensable means for its development process. The roadmap to synthesis resveratrol is as follows:

3,5-dihydroxybenzoic acid (3) forms 3,5-dihydroxybenzoic acid methyl ester (4) by esterification reaction. Choose methyl ether as phenolic hydroxyl-protecting groups. (4) reacts with dimethyl sulfate to get 3,5-di-methoxybenzoate (5). (5) generates the corresponding benzene methanol (6) after reduction, and forms 3, 5-dimethoxy benzyl bromide (7) through further bromination. Then diethyl (3,5-dimethoxy benzyl) phosphonate (8) can be get by roman abramovich's reaction. (8) reacts with p-anisaldehyde to form the key intermediate 3,4,5-trimethoxy-trans-stilbene (9) via Wittig-Honer reaction. Finally, methyl can be removed by freshly prepared aluminum triiodide. Then the aimed product resveratrol can be separated by thin layer chromatography.; View all

9.4 Solubility: Resveratrol is a kinds of natural antioxidants that presents in grapes, red wine, mulberries, peanuts and polygonum cuspidatum. It is polyphenols. It is soluble in organic solvents but insoluble in water. Its dissolved order in organic solvents is: acetone > ethanol> methanol> ethyl acetate> ether> chloroform.

9.5 Possible Side effects: Little is known about the safety of long-term or high dose use of resveratrol.
Since resveratrol might act like estrogen, some medical experts recommend that people with hormone-sensitive cancers (condition such as breast cancer, uterine cancer, ovarian cancer, endometriosis, or uterine fibroids), pregnant women, and children avoid taking resveratrol.
In addition, resveratrol could interact with blood thinners like warfarin, aspirin, and ibuprofen by slow blood clotting, which may increase the risk of bleeding in people with bleeding disorders.
According to one study, high-dose resveratrol supplementation was associated with fever, reduced blood cells, and decreased blood pressure.
There is some concern that high doses of resveratrol supplements could lead to kidney problems in some people.

9.6 Uses

Resveratrol can prevent the oxidation of low density lipoprotein, and has the potential effect on preventing cardiovascular disease, cancer, antivirus and immune regulation. Its main role is antioxidant properties.
Cardiovascular drugs. It can reduce hematic fat and prevent heart disease. It also has the effect on AIDS.
Antioxidants and the activity in anti-inflammatory, antithrombotic, anti-cancer, anti-cancer, anti hyperlipidemia and antibacterial.
Anti-aging, regulating blood lipid, cardiovascular protection, anti-hepatitis.
Resveratrol is a phytoalexin produced naturally by several plants with anti-cancer, anti-inflammatory, blood-sugar-lowering and other beneficial cardiovascular effects.

9.7 Chemical Properties: Off-White to Tan Powder

9.8 Uses: Minor constituent of wine, correlated with serum lipid reduction and inhibition of platelet aggregation. Resveratrol is a specific inhibitor of COX-1, and it also inhibits the hydroperoxidase activity of COX-1. It has been shown to inhibit events associated with tumor initiation, promotion and progression.

9.9 Uses: raw material for Tamiflu; Oseltamivir

9.10 Definition: ChEBI: A resveratrol in which the double bond has E configuration.

9.11 Usage: It is used as a natural phenolic antioxidant that is a potent activator of SIRT1 and inhibitor of Cox-1. Resveratrol has also been used extensively in stem cell studies to enhance self-renewal and multipotency of mesencymal stem cells (MSC?s) in vitro. Resveratrol acts as a NF-κB inhibitor to protect MSC-derived chondrocytes in vitro. Resveratrol is used to treat adipose-derived mesenchymal stem cells (ADMSCs) resulted in increased alkaline phosphatase activity and osteocalcin levels; thus enriching the MSC and osteoprogenitor cell populations in cultured ADMSCs in vitro.

10. Computational chemical data

Molecular Weight: 228.24g/mol
Molecular Formula: C₁₄H₁₂O₃
Compound Is Canonicalized: True
XLogP3-AA: 3.1
Exact Mass: 228.078644241
Monoisotopic Mass: 228.078644241
Complexity: 246
Rotatable Bond Count: 2
Hydrogen Bond Donor Count: 3
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 60.7
Heavy Atom Count: 17
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 1
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBwMAAAAAAAAAAAAAAAAAAAAAAAAAAwYAAAAAAAAAABQAAAGgAACAAADASAmAAwBoAAAgCAAiBCAAACAAAgIAAIiAAGCIgIJyKCERKAcAAlwBUImAeA4BQOIAABCAAAAABAAAIQAAAAAAAAAAAAAA==

11. Question & Answer

What is Resveratrol? Jun 04 2024
Resveratrol Overview Resveratrol is a phytoalexin produced by plants in response to various external influences such as mechanical damage, UV exposure, and fungal attack. It is a key molecule in a fam..
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Introduction: What is Res Zhangratrol and what is its use? Resopratrol, as an antioxidant that naturally exists in a variety of plants, has attracted research and attention in recent years. It is con..
What is the use of resopatrol May 07 2024
Introduction: Resopatrol is a natural antioxidant substance that exists in plants such as grapes, peanuts, and cousin, and has multiple biological activity such as anti -cancer, anti -aging, and immu..
What are the benefits of Resopatrol May 07 2024
Introduction: Resopatrol is a kind of antioxidant that naturally exists in many plants. In recent years, it has attracted much attention and has been widely studied. It is considered to have a variet..

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