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Quercetin dihydrate(CAS No. 6151-25-3)

Quercetin dihydrate C15H10O7?2(H2O) (cas 6151-25-3) Molecular Structure

6151-25-3 Structure

Identification and Related Records

【Name】
Quercetin dihydrate
【Iupac name】
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one dihydrate
【CAS Registry number】
6151-25-3
【Synonyms】
3,3,4,5,7-Pentahydroxyflavone hydrate
3,3,4,5,7-pentahydroxy-2-phenyl-4H-chromen-4-one dihydrate
Quercetin hydrate
3,3,4,5,7-Pentahydroxy-flavone dihydrate
【EINECS(EC#)】
204-187-1
【Molecular Formula】
C15H10O7?2(H2O) (Products with the same molecular formula)
【Molecular Weight】
338.27
【Inchi】
InChI=1/C15H10O7.2H2O/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6;;/h1-5,16-19,21H;2*1H2
【Canonical SMILES】
C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O)O
【MOL File】
6151-25-3.mol

Chemical and Physical Properties

【Appearance】
Yellow solid.
【Melting Point】
300℃
【Boiling Point】
642.4 °C at 760 mmHg
【Flash Point】
642.4 °C at 760 mmHg
【Water】
practically insoluble
【Solubilities】
practically insoluble
【Color/Form】
Yellow needles (dilute alcohol, +2 water)
【Stability】
Stable under normal temperatures and pressures.
【Storage temp】
Keep containers tightly closed. Store in a cool, dry area away from incompatible substances.
【Spectral properties】
MAX ABSORPTION (ALCOHOL): 256 NM (LOG E= 4.32); 301 NM (LOG E= 3.89); 373 NM (LOG E= 4.32); SADTLER REF NUMBER: 594 (IR, PRISM)
IR: 18403 (Sadtler Research Laboratories IR Grating Collection)
UV: 7-578 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
MASS: 14457 (NIST/EPA/MSDC Mass Spectral database, 1990 version)
【Computed Properties】
Molecular Weight:302.2357 [g/mol]
Molecular Formula:C15H10O7
XLogP3:1.5
H-Bond Donor:5
H-Bond Acceptor:7
Rotatable Bond Count:1
Tautomer Count:435
Exact Mass:302.042653
MonoIsotopic Mass:302.042653
Topological Polar Surface Area:127
Heavy Atom Count:22
Formal Charge:0
Complexity:488
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Donor Count:5
Feature 3D Ring Count:3
Effective Rotor Count:1
Conformer Sampling RMSD:0.6
CID Conformer Count:4

Safety and Handling

【Hazard Codes】
T:Toxic
【Risk Statements】
R25
【Safety Statements 】
S45
【HazardClass】
6.1
【Safety】

Poison by ingestion. Experimental reproductive effects. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.?See also QUERCETIN.
Hazard Codes:?ToxicT?
Risk Statements: 25-46-23/24/25?
R25 :Toxic if swallowed.?
R46:May cause heritable genetic damage.?
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.
Safety Statements: 45-53?
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S53:Avoid exposure - obtain special instructions before use.
RIDADR:? UN 2811 6.1/PG 3
WGK Germany:? 3
RTECS:? LK8950000
HazardClass:? 6.1
PackingGroup:? III

【PackingGroup 】
III
【Transport】
UN 2811
【Formulations/Preparations】
Supplied as capsules & tablets
Glycosylated forms include rutin and quercetrin
Intravenous soln in ethanol or DMSO ...
【Specification】

?Quercetin dihydrate , its cas register number is 6151-25-3. It also can be called?3,3',4',5,7-Pentahydroxyflavone dihydrate ; and 2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one dihydrate .?Its classification code are Mutation data and Tumor data.?
?Quercetin dihydrate (CAS NO.6151-25-3) could be stable under normal temperatures and pressures. It is not compatible with strong oxidizing agents, strong acids. And also prevent it to broken down into hazardous decomposition products: carbon monoxide, carbon dioxide, acrid smoke and fumes. In addition, it should keep its containers tightly closed. Or stored in a cool, dry area away from incompatible substances.

【Octanol/Water Partition Coefficient】
log Kow = 1.48 (est)
【Disposal Methods】
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.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Quercetin ... has been obtained for use as a natural coloring agent (Natural Yellow 10) by the rapid extraction of powdered quercitron bark with dilute ammonia and boiling of the extract with sulphuric acid ... The first successful synthesis of quercetin was reported in 1962 ... in which treatment of 2-methoxyacetyl phloroglucinol with O-benzylvanillic acid anhydride in triethylamine and then with potassium hydroxide produced 5,7-dihydroxy-4'-benzyloxy-3,3'- dimethexyflavone. The benzyl ether was cleaved with acetic acid-hydrochloric acid, and the methyl ethers were then cleaved with hydriodic acid to produce quercetin.
Isolation from Rhododendron cinnabarinum Hook, Ericaceae
/Isolation from/ bark of fir trees, also synthetically
【Usage】

Bioflavonoid that provides relieve from chronic pelvic pain syndrome in men.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Naturally occurring or synthetic substances that inhibit or retard the oxidation of a substance to which it is added. They counteract the harmful and damaging effects of oxidation in animal tissues.
【Therapeutic Uses】
Quercetin has been used in medicine to decrease capillary fragility.
/EXPL THER/ ... In a randomized, double-blind, placebo-controlled trial ... /among patients with category III chronic prostatitis syndromes (nonbacterial chronic prostatitis and prostatodynia)/ ... Significant improvement was achieved in the treated group, as measured by the NIH chronic prostatitis score. Some 67% of the treated subjects had at least 25% improvement in symptoms, compared with 20% of the placebo group achieving this same level of improvement. In a follow up, unblind, open-label study ... quercetin was combined with bromelain and papain, which may enhance its absorption. In this study, 82% achieved a minimum 25% improvement score.
/EXPL THER/ Lymphocyte protein kinase phosphorylation was inhibited by quercetin in 9 of 11 cancer patients in a phase I clinical trial. Fifty-one patients with microscopically confirmed cancer not amenable to standard therapies and with a life expectancy of at least 12 wk participated in this trial ... The patients were treated at 3-wk intervals at the beginning of the study. Quercetin was admin iv as quercetin dihydrate ... The max allowed dose was reached when 2 of 3 patients on each dose schedule reached grade 3 or 4 general toxicity, or grad 2 renal toxicity, cardiac toxicity, or neurotoxicity. Phosphorylation was inhibited at 1 hr and persisted for 16 hr. In one patient with ovarian cancer refractory to cisplatin, cancer antigen-125 (CA 125) fell from 295 to 55 units/mL after treatment with 2 courses of quercetin ... A hepatoma patient had serum alpha-fetoprotein fall.
/EXPL THER/ ... Quercetin was reported to inhibit tumor necrosis factor-alpha (TNF-alpha) overproduction and attenuate pathophysiological conditions during acute and chronic inflammation ... In asthma, the activation of mast cells and basophils by allergen releases chemical mediators and synthesizeds cytokines leading to inflammatory conditions ... Quercetin was reported to inhibit cytokine expression and synthesis by human basophils ... A metabolite of quercetin, 3-O-methylquercetin (3-MQ), was reported to provide beneficial effects on asthma by inhibiting cAMP- and cGMP-phosphodiesterase (PDE). ...
【Biomedical Effects and Toxicity】
After oral administration of a single dose of 4 g quercetin to four male and two female volunteers, neither quercetin nor its conjugates was detected in the blood or urine during the first 24 hr; 53% of the dose was recovered in the feces within 72 hr. After a single intravenous injection of 100 mg quercetin to six volunteers, the blood plasma levels declined biphasically, with half-lives of 8.8 min and 2.4 hr; protein binding exceeded 98%. In the urine, 0.65% of the intravenous dose was excreted as unchanged quercetin and 7.4% as a conjugate within 9 hr; no further excretion occurred up to 24 hr ...
When 14C-quercetin was administered orally to ACI rats, about 20% of the administered dose was absorbed from the digestive tract, more than 30% was decomposed to yield 14-CO2 & about 30% was excreted unchanged in feces.. [UENO K ET AL; JPN J EXP MED 53(1): 41 (1983)] PubMed Abstract
One male and one female volunteer were given a diet containing quercetin glucosides (64.2 mg expressed as the aglycone). The mean peak plasma concentration of quercetin was 196 ng/mL which was reached 2.9 hr after ingestion. The time-course of the plasma concentration of quercetin was biphasic, with half-lives of 3.8 hr for the distribution phase and 16.8 hr for the elimination phase. Quercetin was still present in plasma 48 hr after ingestion ... /Quercetin glucosides/
Autoradiographic analysis of a fasted rat 3 hr after administration of a single oral dose of 2.3 mg/kg (4-(14)C)quercetin showed that although most of the radiolabel remained in the digestive tract it also occurred in blood, liver, kidney, lung and ribs. After oral administration of 630 mg/kg of the labelled compound to rats, 34% of the radiolabel excreted within 24 hr ... was expired carbon dioxide, 12% in bile and 9% in urine; within 48 hr, 45% was recovered in the feces. Approximately 60% of the radiolabel in the feces was identified as unmetabolized quercetin ...
About 25% of an ingested dose of quercetin is absorbed from the small intestine and is transported to the liver via the portal circulation, where it undergoes significant first pass metabolism ... Quercetin is strongly bound to albumin in the plasma. Peak levels of plasma quercetin occur from 0.7 to 7 hr following ingestion, and the elimination half-life of quercetin is approx 25 hr.
... The main determinant of absorption of /quercetin glycoside/ conjugates is the nature of the sugar moiety. For example,, quercetin glucoside is absorbed from the small intestine, whereas quercetin rutinoside is absorbed from the colon after removal of the carbohydrate moiety by bacterial enzyme. /Quercetin glycoside conjugates/
Quercetin aglycone and glycones are quite different in their absorption and pharmacokinetics. Studies indicate that the overall kinetic behavior of quercetin changes following the ingestion of quercetin aglycone or glycones. This incl properties such as Cmax (the highest level at a given dose) and Tmax (time to reach Cmax). Currently there are 2 proposed hypotheses on the absorption mechanisms of quercetin glucosides across the small intestine. One is an active uptake of quercetin glucoside by the sodium-dependent glucose transporter (eg, SGLT1) with subsequent deglycosylation within the enterocyte by cytosolic beta-glucosidase (CBG). The other is the absorption by passive diffusion of quercetin after luminal hydrolysis of its glycones by lactase phlorizin hydrolase (LPH). Both methods seem to be utilized for the uptake of individual quercetin glycones with substrate selectivity. For instance, quercetin-4'-glucoside involves both an interaction with SGLT1 and luminal hydrolysis by LPH, whereas quercetin-3-glucoside appears to be absorbed only following hydrolysis by LPH. The deglycosylation step is very critical for the absorption of quercetin glycosides in humans, and is mediated by glucosidases such as LPH and CBG ... Even though the hydrolysis of the glycoside moiety from quercetin glycones is strongly believed to be a prerequisite process for quercetin absorption, there are also reports indicating that a fraction of quercetin may be absorbed as its glycones via passive diffusion and/or unidentified transporters ... /Quercetin conjugates/
... Pharmacokinetic studies suggest that quercetin glycones are absorbed better than its aglycone ... Quercetin glycosides could show significant differences in absorption rate and bioavail, depending on the glycosylation sites ... In the study using quercetin aglycone, it was reported that after a single 4 g dose of quercetin admin orally in humans, the flavonol was detected in the plasma. The highest peak plana concn (Cmax) of quercetin was less than 100 ng/mL, and that all quercetins detected in the plasma were in the form of glucuronidated and sulfated quercetins rather than quercetin aglycone ... following single iv (100 mg) admin of quercetin, the highest peak plasma concn (Cmax) of quercetin was around 3000 ng/mL, and the time to reach Cmax (Tmax) was 10 min ... The sugar moieties and positions of quercetin O-glycosides seem to influence their bioavail as well ... Currently, the avg human intake of quercetin (glycones and aglycone) is less than 60 mg daily. Based on this amt, the highest concn achieved in the plasma (Cmax) is less than 200 ng.mL (0.6 uM), which includes quercetin and all its metabolites ...
... The present study investigates the bioavailability of resveratrol and quercetin in humans, mice, and rats after oral ingestion of grape juice preparations or pure aglycones. Oral administration of resveratrol and quercetin to humans yielded detectable levels of resveratrol, quercetin, and their derivatives in the plasma and urine. Urinary levels of resveratrol, quercetin, and their metabolites were observed in human subjects receiving 600 and 1200 mL of grape juice, whereas quercetin metabolites were identified in urine samples even after receiving 200 mL of grape juice. The cumulative amounts of resveratrol and quercetin excreted in the urine of mice receiving concentrated grape juice for 4 days were 2.3 and 0.7% of the ingested doses, respectively. After i.g. administration of resveratrol to rats (2 mg/kg), up to 1.2 uM resveratrol was observed in the plasma. The study demonstrates that the glycoside forms of resveratrol and quercetin in grape juice are absorbed to a lesser extent than the aglycones. [Meng X et al; J Agric Food Chem 52(4):935-42 (2004)] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 460(SRC), determined from a water solubility of 60 mg/L(2) and a regression-derived equation(3), indicates that quercetin is expected to have moderate mobility in soil(SRC). The estimated pKas of quercetin are 7.17, 8.26, 10.13, 12,30, and 13.11(4), indicating that this compound will partially exist in the anion form in the environment at neutral pH and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of quercetin from moist soil surfaces is not expected to be an important fate process because it is an anion and anions do not volatilize(SRC). Quercetin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.8X10-14 mm Hg(SRC), determined from a fragment constant method(6). Quercetin's rapid degradation in soil(7) suggests that biodegradation may be an important environmental fate process(SRC).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 460(SRC), determined from a water solubility of 60 mg/L(2) and a regression-derived equation(3), indicates that quercetin is not expected to adsorb to suspended solids and sediment(SRC). The estimated pKas of 7.17, 8.26, 10.13, 12,30, and 13.11(4) indicate quercetin will exist partially in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(5). According to a classification scheme(6), an estimated BCF of 61(SRC), from its water solubility(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Quercetin's rapid degradation in soil(7) suggests that biodegradation may be an important environmental fate process in water(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), quercetin, which has an estimated vapor pressure of 2.8X10-14 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase quercetin may be removed from the air by wet or dry deposition(SRC). Quercetin contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

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