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21967-41-9

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21967-41-9 Usage

Description

Different sources of media describe the Description of 21967-41-9 differently. You can refer to the following data:
1. Baicalin, the active compound of the Blue Skullcap, is a type of flavonoid. Baicalin exhibits anti-inflammatory, anti-tumor, anti-angiogenic, anti-oxidant, anti-apoptotic, anti-viral, and antibacterial properties. It could be used for the treatment of autoimmune diseases and several cancers (hepatitis B virus (HBV)-infected liver cancer,? hepatic cancer, cervical cancer, etc.). It can be used to treat against dengue virus. It is used in preparation of the drug for treating and rescuing ricin poisoning. Due to its anti-apoptotic effect which can protect PC-12 cells from oxidative stress, baicalin can be used for reducing stress and helping to promote healthy sleep cycles.
2. Baicalin is a flavonoid that has been found in S. baicalensis and has diverse biological activities. It reduces myocardial apoptosis and increases cardiac microvessel levels of endothelial nitric oxide synthase (eNOS) in a rat model of ischemia-reperfusion injury when administered at doses of 30 and 100 mg/kg. Baicalin (50 and 80 mg/kg) increases the number of intratumor CD8+ T cells and reduces tumor volume in an H22 murine hepatocellular carcinoma model. It reduces LPS-induced cortical production of reactive oxygen species (ROS) and levels of IL-1β and TNF-α in a mouse model of neuroinflammation. Baicalin decreases body weight, increases the number of rats with regular estrous cycles, and ameliorates follicular development in a mouse model of dehydroepiandrosterone-induced polycystic ovary syndrome (PCOS). It also decreases immobility time in the forced swim test in a mouse model of depression induced by chronic mild stress.
3. Baicalin is one of the main active ingredients obtained from the roots of huang qin (Scutellaria baicalensis Georgi). The Pharmacopoeia of the People’s Republic of China (2015) stipulates that the content of baicalin in radix scutellariae with dry goods shall not be less than 9.0%. The medicinal radix scutellariae distribution in China are now Yunnan radix scutellariae (S. amoena C.?H. Wright), sticky hairs radix scutellariae (S. viscidula Bunge), Gansu radix scutellariae (S. rehderiana Diels), Lijiang radix scutellariae (S. likiangensis Diels), Sichuan radix scutellariae (S. hypericifolia Lev l.), radix scutellariae (S. tenax W.?W. Smith var. patentipilosa G.? Y. Wu), etc., which contain a certain amount of baicalin. Radix scutellariae medicinal has a long history in China. Listed as goods in Shen Nong’s Classic of Materia Medica, it has been used clinically to treat diseases with symptoms such as “heat jaundice, intestinal dysentery, edema, amenorrhea, malignant sore, and scleritis” for about 2000? years. Scutellaria is recorded in the Pharmacopoeia of the People’s Republic of China to have the effects of “clear heat and wet, purging fire to detoxify, stop bleeding and tocolysis.” It is one of the commonly used traditional Chinese herbs, which is clinically used alone or with other Chinese medicine compatibility for the treatment of respiratory infections, acute dysentery, viral hepatitis, allergic disease and gynecological disease, and so on.

References

[1] Ehsan Moghaddam, Boon-Teong Teoh, Sing-Sin Sam, Rafidah Lani, Pouya Hassandarvish, Zamri Chik, Andrew Yueh, Sazaly Abubakar, Keivan Zandi (2014) Baicalin, a metabolite of baicalein with antiviral activity against dengue virus, Scientific Reports, 4, 5452 [2] Yuan Zhang, Xing Li, Bogoljub Ciric, Cun-Gen Ma, Bruno Gran, Abdolmohamad Rostami, Guang-Xian Zhang (2015) Therapeutic effect of baicalin on experimental autoimmune encephalomyelitis is mediated by SOCS3 regulatory pathway, Scientific Reports, 5, 17407 [3] Patent US 20160361334 A1: Application of baicalin in preparation of drug for treating ricin poisoning

Chemical Properties

Light yellow powder

Physical properties

Appearance: light yellow crystalline powder at room temperature. Solubility: insoluble in methanol, ethanol, and acetone; slightly soluble in chloroform and nitrobenzene; almost insoluble in water; soluble in hot acetic acid. Melting point: 202–205?°C.

History

The chemical research of the genus Scutellaria began in 1889. Baicalein (scutellarein) is the first flavonoid isolated from Vietnam radix scutellariae (S. altissima) in 1910. In 1922, Shibata Gui Tai and his collaborators isolated and obtained baicalin, baicalein, wogonin, and benzoic acid from Scutellaria baicalensis.Among the flavonoids in Scutellaria baicalensis, the content of baicalein is the highest. Its official name is baikeli. Baicalin is formed by the combination of baicalein and one molecule of glucuronic acid. Both baicalein and baicalin exist in Scutellaria baicalensis. Studies showed that baicalein could be transferred into baicalin and other metabolites in the blood. However, baicalin by oral is hardly absorbed. Baicalein can be absorbed and also rapidly converted into baicalin.At present, there are a variety of mature extraction methods for obtaining baicalin and baicalein from Scutellaria baicalensis. Due to the poor water solubility, oral preparation of baicalin is mostly used in clinical practice. Research showed that baicalin had a significant first pass effect, which led to its low bioavailability. Baicalin-metal complexes formed by the combination of baicalin and metal ions were found to enhance bioavailability and increase pharmacological activities. In addition, the preparation of ester-type prednisone was easily hydrolyzed by esterase and could improve the lipid solubility of baicalin.

Uses

Different sources of media describe the Uses of 21967-41-9 differently. You can refer to the following data:
1. diuretic, prolyl endopeptidase inhibitor, antineoplastic
2. Baicalin has been used in a study to examine its neuroprotective effect in chronically stressed rats.2

Definition

ChEBI: The glycosyloxyflavone which is the 7-O-glucuronide of baicalein.

Indications

Baicalin is mainly used for the adjuvant therapy of acute and chronic hepatitis and persistent hepatitis.

General Description

Baicalin is a key flavonoid found in the roots of Scutellaria baicalensis. It is known to have different biological activities, such as anti-oxidative, anti-inflammatory, antitumor and anti-apoptotic activities.

Pharmacology

Pharmacological studies showed that both baicalein and baicalin had a variety of pharmacological effects such as antibacterial, antiviral, removal of oxygen free radicals, antioxidant, antipyretic, analgesic, anti-inflammatory, antitumor, cardiovascular protecting, cerebrovascular and neuron protecting, liver protecting, and prevention or treatment of diabetes and its complications1. Antibacterial and antiviral effects: Scutellaria baicalensis was reported to have growth inhibitory effect on a variety of Gram-negative bacteria, Gram-positive bacteria, and spirochetes, showing a broad antibacterial spectrum. Baicalein was regarded as the main ingredient in Scutellaria baicalensis to play the antibacterial effect. The IC50 of baicalein on Escherichia coli was about 0.29?mmol·L?1 , and the minimum inhibitory concentration (MICs) of Candida albicans was 264?μg·mL?1 . The survival time of mice infected with influenza virus was significantly extended by the gastric irrigation of baicalin at a dose of 0.96–1.5?g·kg?1.2. Antitumor effect: In vitro and in vivo experimental results showed that both baicalein and baicalin had obvious antitumor activity, and the mechanism involved the inhibition of tumor cell proliferation, invasion and metastasis, induction of tumor cell apoptosis, suppression of neovascularization, and enhanced tumor cell chemotherapy sensitivity. Baicalein was found to inhibit theproliferation of rat bladder cancer MBT-2 cells and induce apoptosis, and its IC50 was 0.43?μmol·L?1 . In bladder cancer model formed by injection of MBT-2 cells into C3H/HeN nude mice, the formed tumor in mouse given baicalein 0.05– 0.1?mg·day?1 for ten consecutive days was significantly smaller than that of the control group. A 50–200?μmol·L?1 baicalein could inhibit the proliferation of human prostate cancer DU2145 and PC3 cells, human umbilical vein endothelial cell proliferation, and the formation of buds and vascular structure in a dosedependent manner. Baicalein could also inhibit human breast cancer cell MDAMB-231 adhesion, metastasis, and invasion, in a dose-dependent manner in the range of 2–50?μmol·L?1 . Moreover, a dose of 100?μg·mL?1 could also reverse the resistance of ovarian cancer cell line A2780/ADM.?This reversal may be associated with a decrease in P-gp drug efflux and increased intracellular drug concentration3. Antipyretic, analgesic, and anti-inflammatory effects: Both baicalein and baicalin can play antipyretic, analgesic, and anti-inflammatory effects by interfering with the arachidonic acid metabolism pathway, inhibiting the activity of nuclear factor, and suppressing the secretion and release. In rats, intraperitoneal injection of baicalin at a dose of 4.5?mg·kg?1 could exert antipyretic effect; the body temperature of the endotoxin-induced fever rabbits was heavily reduced after intravenous administration of baicalin at a dose of 20?mg·kg?1 ; baicalein at a dose of 20?mg·kg?1 (iv) could improve the hemodynamics and heart rate and reduce the mortality and the leukocyte infiltration into the liver and lung tissues in endotoxic shock rats (LPS 10?mg·kg?1 , iv).4. Scavenging oxygen free radicals and antioxidant effects: Both baicalein and baicalin were found to have strong scavenging effects on hydroxyl radicals, superoxide anion (O2?), alkane peroxy radicals, and DPPH free radicals. A 25–100?μmol·L?1 baicalein can inhibit H2O2-induced RAW264.7 cell apoptosis and diploid formation.5. Liver protection: Both baicalein and baicalin were found to have protective effect on the liver injured by a variety of causes, and the mechanism was related to their function of antioxidant and inhibition of the secretion of inflammatory mediators. It was found that intraperitoneal injection of baicalin at a dose of 50–200?mg·kg?1 had protective effect on CCl4-induced acute liver injury mice. Intraperitoneal injection of baicalin at a dose of 70?mg·kg?1 could improve CCl4- induced chronic liver fibrosis in mice. In addition, gavage of baicalin to mice at a dose of 50–150?mg·kg?1 significantly reduced the immune liver injury caused by D-GalN and LPS.6. Treatment or prevention of diabetes and its complications: Baicalein was found to have effects of protecting the islet tissue and improving kidney function and retinopathy in diabetic rats, and the mechanism might ascribe to its function on reducing the inflammatory response and inhibition of oxidative stress injury. Streptozotocin-induced diabetic rats were found to have decreased blood glucose concentration and the improvement of islet tissue damage after gavage of baicalin at a dose of 25–100? mg·kg?1 . After gavage of baicalin at a dose of 80–120?mg·kg?1 for 12?weeks, an obvious protective effect on the kidney tissueof diabetic rats was observed. In addition, the administration of baicalein at a dose of 150?mg·kg?1 day?1 was found to ameliorate diabetic retinopathy.7. Cardiovascular and cerebrovascular protective effects: In vitro experiment results showed that Scutellaria baicalensis had cardiovascular protective effects such as dilating blood vessels, counteracting high blood pressure, protecting heart and endothelial cells, and anti-atherosclerosis. Baicalein did not affect normal blood pressure in rats but could reduce blood pressure in hypertensive rats. Baicalin at concentration of 0.5 and 2?μmol·L?1 was found to decrease the contractile tension of isolated rat aorta induced by norepinephrine, KCl, and CaCl2, shifting the reaction curve from the left to the right side and reducing the maximal effect. It could also significantly inhibit the norepinephrine-dependent contraction induced by intracellular and outside Ca2+. Baicalein had protective effect on myocardial ischemia and reperfusion injury, and this effect was stronger than baicalin. Intravenous injection of baicalein at a dose of 10?mg·kg?1 could improve the contraction of myocardium in endotoxic shock rats.8. Neuroprotective effect: Baicalein had a good neuroprotective effect. It could suppress nerve injury and apoptosis by inhibiting the inflammatory response induced by glial cell, anti-free radicals, and protection of mitochondria. Administration of baicalein at a dose of 200?mg·kg?1 could relieve 6-OHDAinduced muscle tremor injury in rats. Gavage of baicalein at a dose of 200?mg·kg?1 could improve the recovery of motor function in Parkinson model mice induced by 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP). Intraperitoneal injection of baicalein at a dose of 30?mg·kg?1 reduced the neurological deficit score of MCAO model rats, decreasing brain water content and cerebral infarction volume, which indicated that baicalein had a protective effect on the neurological function of rats with focal cerebral ischemia.9. Other effects: Baicalein and baicalin were also reported to have other pharmacological effects such as enhancing immune function.

Clinical Use

In clinical, baicalin is mainly used as the adjuvant therapy for acute and chronic hepatitis and persistent hepatitis. Baicalin was shown to reduce the expression of hepatitis B surface antigen, e antigen and the core antigen, and inhibited hepatitis B virus DNA replication. Reduced serum alanine aminotransferase level was observed in hepatitis patient treated with baicalin, and other liver function indexes were also found to be improved. No adverse reactions about baicalin have been reported. In addition, baicalin was reported to treat early diabetic nephropathy and alleviate the symptoms of diabetic neuropathyAs one of the antimicrobial components of Scutellaria baicalensis, eye drops containing 3% baicalin are used clinically in the treatment of trachoma, with the similar curative effect as rifampicin.Moreover, baicalein is used clinically for the treatment of enteritis and dysentery.

Enzyme inhibitor

This baicalein glucuronide (FW = 446.36 g/mol; CAS 21967-41-9), also known as 5,6-dihydroxy-4-oxygen-2-phenyl-4H-1-benzopyran-7-b-D glucopyranose acid, is a flavone prodrug found in the Chinese medicinal herb Huang-chin (Scutellaria baicalensis) that is hydrolyzed to baicalein (See Baicalein). Baicalin is a slow, tight-binding inhibitor of Jack Bean urease, rapidly forming initial BA-urease complex (Ki = 3.9 × 10–3 M) that slowly isomerizes to the final complex (overall inhibition constant of Ki* = 0.15 × 10 μM. Inhibition can be reversed by dithiothreitol but not dilution of substrate. Baicalin also inhibits prolyl oligopeptidase, a cytosolic serine peptidase that hydrolyzes proline-containing peptides at the carboxy terminus of proline residues and is associated with schizophrenia, bipolar affective disorder, and related neuropsychiatric disorders. (See Pramiracetam)

Check Digit Verification of cas no

The CAS Registry Mumber 21967-41-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,1,9,6 and 7 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 21967-41:
(7*2)+(6*1)+(5*9)+(4*6)+(3*7)+(2*4)+(1*1)=119
119 % 10 = 9
So 21967-41-9 is a valid CAS Registry Number.
InChI:InChI=1/C21H18O11/c22-9-6-10(8-4-2-1-3-5-8)30-11-7-12(14(23)15(24)13(9)11)31-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-7,16-19,21,23-27H,(H,28,29)

21967-41-9 Well-known Company Product Price

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  • TCI America

  • (B2835)  Baicalin  >90.0%(T)

  • 21967-41-9

  • 25g

  • 1,290.00CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001273)  Baicalin  European Pharmacopoeia (EP) Reference Standard

  • 21967-41-9

  • Y0001273

  • 1,880.19CNY

  • Detail
  • Aldrich

  • (572667)  Baicalin  95%

  • 21967-41-9

  • 572667-1G

  • 1,938.69CNY

  • Detail

21967-41-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name baicalin

1.2 Other means of identification

Product number -
Other names BAICALIN

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
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More Details:21967-41-9 SDS

21967-41-9Synthetic route

5,6-Diacetoxy-7-hydroxyflavon-7-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosiduronsaeure-methylester)
74304-67-9

5,6-Diacetoxy-7-hydroxyflavon-7-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosiduronsaeure-methylester)

baicalin
21967-41-9

baicalin

5,6,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one
491-67-8

5,6,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one

UDP-glucuronic acid
2616-64-0

UDP-glucuronic acid

baicalin
21967-41-9

baicalin

Conditions
ConditionsYield
With Tris-HCl buffer; UDP-glucuronate: baicalein 7-O-glucuronosyltransferase In water at 37℃; pH=7.5; Enzyme kinetics; Esterification; Enzymatic reaction;
4-oxo-2-phenyl-4H-1-benzopyran-5,6,7-triyl triacetate
67047-05-6

4-oxo-2-phenyl-4H-1-benzopyran-5,6,7-triyl triacetate

baicalin
21967-41-9

baicalin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 68 percent / K2CO3, KI / acetone / 4 h / Heating
2: 60 percent / H2 / Pd/C / acetone
3: 41 percent
View Scheme
(3R,4S,5S,6S)-2-bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
57820-69-6

(3R,4S,5S,6S)-2-bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

baicalin
21967-41-9

baicalin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 41 percent
View Scheme
5,6-diacetoxy-7-hydroxyflavone
67047-07-8

5,6-diacetoxy-7-hydroxyflavone

baicalin
21967-41-9

baicalin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 41 percent
View Scheme
7-(benzyloxy)-4-oxo-2-phenyl-4H-1-benzopyran-5,6-diyl diacetate
67047-06-7

7-(benzyloxy)-4-oxo-2-phenyl-4H-1-benzopyran-5,6-diyl diacetate

baicalin
21967-41-9

baicalin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 60 percent / H2 / Pd/C / acetone
2: 41 percent
View Scheme
C21H18O11*C42H70O35
1178862-93-5

C21H18O11*C42H70O35

A

baicalin
21967-41-9

baicalin

B

β‐cyclodextrin
7585-39-9

β‐cyclodextrin

Conditions
ConditionsYield
In water at 20℃; Equilibrium constant;
chlorosulfite de methyle
13165-72-5

chlorosulfite de methyle

baicalin
21967-41-9

baicalin

Baicalin methyl ester
82475-03-4

Baicalin methyl ester

Conditions
ConditionsYield
In methanol at 20℃; for 8.5h; Inert atmosphere;96.1%
at 25℃; for 10h; Time;
zinc diacetate
557-34-6

zinc diacetate

water
7732-18-5

water

sodium acetate
127-09-3

sodium acetate

acetic acid
64-19-7

acetic acid

baicalin
21967-41-9

baicalin

C25H26O17Zn(2-)*Na(1+)

C25H26O17Zn(2-)*Na(1+)

Conditions
ConditionsYield
at 63℃; for 0.95h; pH=5.8; Temperature; pH-value;96.06%
aluminum (III) chloride
7446-70-0, 7784-13-6

aluminum (III) chloride

baicalin
21967-41-9

baicalin

C42H34AlO22

C42H34AlO22

Conditions
ConditionsYield
In aq. acetate buffer at 63℃; for 0.95h; pH=5.8; pH-value; Temperature;95.87%
methanol
67-56-1

methanol

baicalin
21967-41-9

baicalin

Baicalin methyl ester
82475-03-4

Baicalin methyl ester

Conditions
ConditionsYield
With sulfuric acid for 1h; Heating;95%
With sulfuric acid In tetrahydrofuran at 80℃; for 6h;95%
With sulfuric acid In tetrahydrofuran; methanol at 80℃; for 6h;95%
aluminum(III) sulfate

aluminum(III) sulfate

baicalin
21967-41-9

baicalin

C42H34AlO22

C42H34AlO22

Conditions
ConditionsYield
In aq. acetate buffer at 65℃; for 1.33333h; pH=6; pH-value; Temperature;94.82%
aluminum acetate
139-12-8

aluminum acetate

baicalin
21967-41-9

baicalin

C42H34AlO22

C42H34AlO22

Conditions
ConditionsYield
In aq. acetate buffer at 50℃; for 1h; pH=5; pH-value; Temperature;94.38%
baicalin
21967-41-9

baicalin

5,6,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one
491-67-8

5,6,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one

Conditions
ConditionsYield
With sulfuric acid; water at 20℃; for 0.166667h;93%
With sulfuric acid In water at 90℃; for 0.0833333h;71.9%
With sulfuric acid at 90℃; for 0.166667h;29.3%
methoxypolyethylene glycol ethylamine

methoxypolyethylene glycol ethylamine

baicalin
21967-41-9

baicalin

conjugate of methoxy-polyethylene glycol and baicalin

conjugate of methoxy-polyethylene glycol and baicalin

Conditions
ConditionsYield
With dmap; benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 20℃;92%
baicalin
21967-41-9

baicalin

butan-1-ol
71-36-3

butan-1-ol

baicalin butyl ester

baicalin butyl ester

Conditions
ConditionsYield
With thionyl chloride at 0 - 40℃; for 14h;77%
With Novozym 435 (Candida antarctica lipase B immobilized on a hydrophobic carrier acrylic resin) In pyridine; cyclohexane at 50℃; for 120h; Molecular sieve; Enzymatic reaction;
ethanol
64-17-5

ethanol

baicalin
21967-41-9

baicalin

baicalein 7-O-β-D-ethylglucuronide

baicalein 7-O-β-D-ethylglucuronide

Conditions
ConditionsYield
With thionyl chloride at 0 - 20℃; for 14h;76%
With sulfuric acid Reflux; Inert atmosphere;
With Novozym 435 (Candida antarctica lipase B immobilized on a hydrophobic carrier acrylic resin) In pyridine; cyclohexane at 50℃; for 120h; Molecular sieve; Enzymatic reaction;
propan-1-ol
71-23-8

propan-1-ol

baicalin
21967-41-9

baicalin

baicalin propyl ester

baicalin propyl ester

Conditions
ConditionsYield
With thionyl chloride at 0 - 20℃; for 14h;71%
With Novozym 435 (Candida antarctica lipase B immobilized on a hydrophobic carrier acrylic resin) In pyridine; cyclohexane at 50℃; for 120h; Molecular sieve; Enzymatic reaction;
n-heptan1ol
111-70-6

n-heptan1ol

baicalin
21967-41-9

baicalin

baicalin heptyl ester

baicalin heptyl ester

Conditions
ConditionsYield
With thionyl chloride at 0 - 60℃; for 14h;65%
baicalin
21967-41-9

baicalin

C21H14(2)H4O11

C21H14(2)H4O11

Conditions
ConditionsYield
Stage #1: baicalin With [D]-sodium hydroxide; platinum on activated charcoal; water-d2 at 130℃; for 12h; Inert atmosphere;
Stage #2: With formic acid at 130℃; for 1h; Inert atmosphere;
65%
baicalin
21967-41-9

baicalin

oroxylin A
480-11-5

oroxylin A

Conditions
ConditionsYield
Stage #1: baicalin With potassium carbonate; dimethyl sulfate at 20℃; for 24h;
Stage #2: With hydrogenchloride In ethanol
56%
Stage #1: baicalin With potassium carbonate; dimethyl sulfate at 20℃;
Stage #2: With hydrogenchloride In ethanol at 80℃; for 10h;
56%
Multi-step reaction with 6 steps
1: water; sulfuric acid / 0.67 h / 121 °C
2: sodium acetate / 0.67 h / 40 °C
3: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C
4: water; sodium hydroxide; sodium dithionite / methanol / 16 h / 20 °C
5: potassium carbonate / N,N-dimethyl-formamide / 21 h / 20 °C
6: water; hydrogenchloride / N,N-dimethyl-formamide / 0.17 h / 20 °C
View Scheme
dimethyl sulfate
77-78-1

dimethyl sulfate

baicalin
21967-41-9

baicalin

oroxylin A
480-11-5

oroxylin A

Conditions
ConditionsYield
Stage #1: dimethyl sulfate; baicalin With potassium carbonate at 20℃; for 24h;
Stage #2: With hydrogenchloride In ethanol; water at 80℃;
56%
9-O-(4-bromoethane)berberine hydrochloride

9-O-(4-bromoethane)berberine hydrochloride

baicalin
21967-41-9

baicalin

C44H40NO15(1+)

C44H40NO15(1+)

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 86℃; for 0.75h;53%
methanol
67-56-1

methanol

baicalin
21967-41-9

baicalin

5,6-dihydroxy-7-methoxyflavone
29550-13-8

5,6-dihydroxy-7-methoxyflavone

Conditions
ConditionsYield
Stage #1: methanol; baicalin With sulfuric acid for 2h; Reflux; Inert atmosphere;
Stage #2: With sodium tetrahydroborate at 20℃; for 48h; Inert atmosphere;
51%
pentan-1-ol
71-41-0

pentan-1-ol

baicalin
21967-41-9

baicalin

baicalin pentyl ester

baicalin pentyl ester

Conditions
ConditionsYield
With thionyl chloride at 0 - 40℃; for 14h;39%
acetic anhydride
108-24-7

acetic anhydride

baicalin
21967-41-9

baicalin

4,5,6,7-tetra-O-acetylflavone
1180-46-7

4,5,6,7-tetra-O-acetylflavone

Conditions
ConditionsYield
With pyridine at 60℃; for 48h; Inert atmosphere;35.7%
baicalin
21967-41-9

baicalin

hexan-1-ol
111-27-3

hexan-1-ol

baicalin hexyl ester

baicalin hexyl ester

Conditions
ConditionsYield
With thionyl chloride at 0 - 40℃; for 14h;27%
With Novozym 435 (Candida antarctica lipase B immobilized on a hydrophobic carrier acrylic resin) In pyridine; cyclohexane at 50℃; for 120h; Molecular sieve; Enzymatic reaction;
benzoyl chloride
98-88-4

benzoyl chloride

baicalin
21967-41-9

baicalin

O2,O4-dibenzoyl-O1-(5,6-bis-benzoyloxy-4-oxo-2-phenyl-4H-chromen-7-yl)-β-D-glucopyranuronic acid-lactone

O2,O4-dibenzoyl-O1-(5,6-bis-benzoyloxy-4-oxo-2-phenyl-4H-chromen-7-yl)-β-D-glucopyranuronic acid-lactone

Conditions
ConditionsYield
With pyridine
baicalin
21967-41-9

baicalin

A

O2,O4-diacetyl-O1-(5,6-diacetoxy-4-oxo-2-phenyl-4H-chromen-7-yl)-β-D-glucopyranuronic acid-lactone

O2,O4-diacetyl-O1-(5,6-diacetoxy-4-oxo-2-phenyl-4H-chromen-7-yl)-β-D-glucopyranuronic acid-lactone

B

O2,O3,O4-triacetyl-O1-(5,6-diacetoxy-4-oxo-2-phenyl-4H-chromen-7-yl)-β-D-glucopyranuronic acid

O2,O3,O4-triacetyl-O1-(5,6-diacetoxy-4-oxo-2-phenyl-4H-chromen-7-yl)-β-D-glucopyranuronic acid

Conditions
ConditionsYield
With sodium acetate; acetic anhydride
baicalin
21967-41-9

baicalin

A

Baicalein-6-O-β-D-glucopyranosiduronsaeure
35990-03-5

Baicalein-6-O-β-D-glucopyranosiduronsaeure

B

6-O-β-glucopyranuronosyl-baicalein 7-O-sulfate
126527-77-3

6-O-β-glucopyranuronosyl-baicalein 7-O-sulfate

C

baicalein-6-O-β-D-glucopyranuronoside-7-O-β-D-glucopyranuronoside
126553-37-5

baicalein-6-O-β-D-glucopyranuronoside-7-O-β-D-glucopyranuronoside

D

oroxyloside
36948-76-2

oroxyloside

Conditions
ConditionsYield
by metabolism in rats;A 5 mg
B 15 mg
C 60 mg
D 4 mg
by metabolism in rats;A 5 mg
B 15 mg
C 60 mg
D 2 mg
bromine
7726-95-6

bromine

acetic acid
64-19-7

acetic acid

baicalin
21967-41-9

baicalin

dibromo derivative C21H16Br2O11

dibromo derivative C21H16Br2O11

sodium acetate
127-09-3

sodium acetate

acetic anhydride
108-24-7

acetic anhydride

baicalin
21967-41-9

baicalin

A

O2,O4-diacetyl-O1-<5,6-diacetoxy-4-oxo-2-phenyl-4H-chromen-7-yl>-β-D-glucopyranuronic acid-3-lactone

O2,O4-diacetyl-O1-<5,6-diacetoxy-4-oxo-2-phenyl-4H-chromen-7-yl>-β-D-glucopyranuronic acid-3-lactone

B

penta-O-acetyl-baicalin

penta-O-acetyl-baicalin

dimethyl sulfate
77-78-1

dimethyl sulfate

baicalin
21967-41-9

baicalin

5-hydroxy-6-methoxyflavone-7-O-β-D-glucuronide methyl ester
82475-02-3

5-hydroxy-6-methoxyflavone-7-O-β-D-glucuronide methyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide; acetone for 3h; Heating;

21967-41-9Relevant articles and documents

Identification of flavone glucuronide isomers by metal complexation and tandem mass spectrometry: Regioselectivity of uridine 5′-diphosphate- glucuronosyltransferase isozymes in the biotransformation of flavones

Robotham, Scott A.,Brodbelt, Jennifer S.

, p. 1457 - 1463 (2013)

Flavone glucuronide isomers of five flavones (chrysin, apigenin, luteolin, baicalein, and scutellarein) were differentiated by collision-induced dissociation of [Co(II) (flavone-H) (4,7-diphenyl-1,10-phenanthroline) 2]+ complexes. The complexes were generated via postcolumn addition of a metal-ligand solution after separation of the glucuronide products generated upon incubation of each flavone with an array of uridine 5′-diphosphate (UDP)-glucuronosyltransferase (UGT) isozymes. Elucidation of the glucuronide isomers allowed a systematic investigation of the regioselectivity of 12 human UGT isozymes, including 8 UGT1A and 4 UGT2B isozymes. Glucuronidation of the 7-OH position was the preferred site for all the flavones except for luteolin, which possessed adjacent hydroxyl groups on the B ring. For all flavones and UGT isozymes, glucuronidation of the 5-OH position was never observed. As confirmed by the metal complexation/MS/MS strategy, glucuronidation of the 6-OH position only occurred for baicalein and scutellarein when incubated with three of the UGT isozymes.

Preparation and characterization of the inclusion complex of Baicalin (BG) with β-CD and HP-β-CD in solution: An antioxidant ability study

Li, Jinxia,Zhang, Min,Chao, Jianbin,Shuang, Shaomin

scheme or table, p. 752 - 756 (2009/09/26)

The formation of the complexes of BG with β-CD and HP-β-CD was studied by UV-vis absorption spectroscopy, fluorescence spectra, Phase-solubility measurements and nuclear magnetic resonance spectroscopy (NMR) in solution. The formation constants (K) of com

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