Baicalein

Iupac Name：5,6,7-trihydroxy-2-phenylchromen-4-one

Molecular Weight：270.23700

Modify Date.: 2022-11-22 22:15

Introduction:

An inhibitor of 12-lipoxygenase, leukotriene biosynthesis and release of lysosomal enzymes. It also inhibits cellular Ca2+ uptake and mobilization and adjuvant-induced arthritis. Baicalein is the flavonoid component of Nepalese and Sino-Japanese crude d

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1. Names and Identifiers

1.1 Name: Baicalein
1.2 Synonyms: 4H-1-BENZOPYRAN-4-ONE,5,6,7-TRIHYDROXY-2-PHENYL 5,6,7-trihydroxy-2-phenyl-4-chromenone hydrate 5,6,7-trihydroxy-2-phenyl-4H-chroMen-4-one 5,6,7-TRIHYDROXYFLAVONE BAICALEIN(SH)NOW RG GRADE Baicalein, monohydrate, 5,6,7-Trihydroxy-2-phenyl-4H-chromen-4-one monohydrate Baicaleine Baicalin Baicelein MFCD00017459 Noroxylin

1.3 CAS No.: 491-67-8

1.4 CID: 5281605

1.5 EINECS(EC#): 000-000-0

1.6 Molecular Formula: C15H10O5 (isomer)

1.7 Inchi: InChI=1S/C15H10O5/c16-9-6-11(8-4-2-1-3-5-8)20-12-7-10(17)14(18)15(19)13(9)12/h1-7,17-19H

1.8 InChkey: FXNFHKRTJBSTCS-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C=C(C(=C3O)O)O

1.10 Isomers Smiles: C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C=C(C(=C3O)O)O

2. Properties

2.1 Density: 1.548 g/cm3

2.1 Melting point: 256-271°C(lit.)

2.1 Boiling point: 575.9ºC at 760 mmHg

2.1 Refractive index: 1.5000 (estimate)

2.1 Flash Point: 225.2ºC

2.1 Precise Quality: 270.05300

2.1 PSA: 90.90000

2.1 logP: 2.57680

2.1 Solubility: Soluble to 50 mM in DMSO

2.2 Appearance: Yellow Crystalline Solid

2.3 Storage: Ambient temperatures.

2.4 Chemical Properties: Yellow Crystalline Solid

2.5 Color/Form: Yellow powder

2.6 pKa: 6.31±0.40(Predicted)

2.7 Water Solubility: Soluble to 50 mM in DMSO

2.8 StorageTemp: Keep in dark place,Sealed in dry,2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A trihydroxyflavone with the hydroxy groups at positions C-5, -6 and -7.

3.2 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 34 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 6 of 34 companies. For more detailed information, please visit ECHA C&L website

Of the 5 notification(s) provided by 28 of 34 companies with hazard statement code(s):

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (96.43%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501

3.3 Usage: An inhibitor of 12-lipoxygenase, leukotriene biosynthesis and release of lysosomal enzymes. It also inhibits cellular Ca2+ uptake and mobilization and adjuvant-induced arthritis. Baicalein is the flavonoid component of Nepalese and Sino-Japanese crude d

4. Safety and Handling

4.1 Symbol: GHS07

4.1 Hazard Codes: Xi

4.1 Signal Word: Warning

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S26-S36

4.1 Hazard Declaration: H315-H319-H335

4.1 RIDADR: NONH for all modes of transport

4.1 Caution Statement: P261-P305 + P351 + P338

4.1 WGK Germany: 3

4.1 RTECS: DJ3100898

4.1 Safety: Hazard Codes:Xi,Xn
Risk Statements:36/37/38-20/21/22
36/37/38:Irritating to eyes, respiratory system and skin
20/21/22:Harmful by inhalation, in contact with skin and if swallowed
Safety Statements:26-36
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:Wear suitable protective clothing
WGK Germany:3
Hazard Note:Irritant

4.2 Specification: Yellow Crystalline Solid
usageEng:An inhibitor of 12-lipoxygenase, leukotriene biosynthesis and release of lysosomal enzymes. It also inhibits cellular Ca2+ uptake and mobilization and adjuvant-induced arthritis. Baicalein is the flavonoid component of Nepalese and Sino-Japanese crude d
Safety Statements:26-36
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:Wear suitable protective clothing

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. 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. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. Synthesis Route

491-67-8Total: 30 Synthesis Route

93-97-0 147 Suppliers

491-67-8 238 Suppliers

Literatures:
Sastri; Seshadri Proceedings - Indian Academy of Sciences, Section A, 1946 , # 23 p. 273,276
Yield: null

973-67-1 12 Suppliers

491-67-8 238 Suppliers

Literatures:
Kim, Dong Han; Yun, Chang Hyeon; Kim, Min Hwan; Naveen Kumar, Ch.; Yun, Bo Hee; Shin, Ji-Sun; An, Hyo Jin; Lee, Young Hun; Yun, Yong Don; Rim, Hong-Kun; Yoo, Min-Sang; Lee, Kyung-Tae; Lee, Yong Sup Bioorganic and Medicinal Chemistry Letters, 2012 , vol. 22, # 1 p. 700 - 705
Yield: ~93%

480-11-5 52 Suppliers

491-67-8 238 Suppliers

Literatures:
Waghmode, Suresh B.; Mahale, Ganesh; Patil, Viraj P.; Renalson, Kartik; Singh, Dharmendra Synthetic Communications, 2013 , vol. 43, # 24 p. 3272 - 3280
Yield: ~83%

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7. Precursor and Product

precursor:

35990-03-5

119892-40-9

57396-78-8

21967-41-9

93-97-0

70185-52-3

67047-05-6

6962-57-8

571168-66-6

642-71-7

126553-37-5

621-82-9

520-28-5

7499-99-2

480-11-5

3316-54-9

632-85-9

29550-13-8

973-67-1

22248-14-2

6959-90-6

742073-28-5

28279-72-3

102-92-1

126527-77-3

View all

product :

740-33-0

29550-13-8

973-67-1

21967-41-9

480-11-5

2035-05-4

73202-52-5

8. Other Information

8.0 Target: Value

8.1 General Description: Baicalein, a flavonoid, is a xanthine oxidase inhibitor. Anti-inflammatory effects of baicalein in peripheral human leukocytes has been studied.

8.2 Merck: 14,942

8.3 BRN: 272683

8.4 Chemical Properties: Yellow Crystalline Solid

8.5 Uses: antiviral (HIV)

8.6 Uses: An inhibitor of 12-lipoxygenase, leukotriene biosynthesis and release of lysosomal enzymes. It also inhibits cellular Ca2+ uptake and mobilization and adjuvant-induced arthritis. Baicalein is the fl avonoid component of Nepalese and Sino-Japanese crude drugs.

8.7 Uses: inhibitor of lipoxidase and leukotriene biosynthesis

8.8 Uses: An inhibitor of Ca2+ uptake, 5-LO, and 12-LO

8.9 Definition: ChEBI: A trihydroxyflavone with the hydroxy groups at positions C-5, -6 and -7.

8.10 Biological Activity: Inhibitor of 5- and platelet 12-lipoxygenases (IC 50 values are 9.5 and 0.12 mM respectively). Also inhibits Raf-mediated MEK-1 phosphorylation in C6 rat glioma cells and induces G1 and G2 cell cycle arrest by decreasing cdk1, cdk2, cyclin D2 and cyclin A expression. Anti-inflammatory in vivo .

8.11 Collision Cross Section: 153.8 ?2 [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

8.12 Mesh: Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)|Compounds that inhibit the action of prostaglandins. (See all compounds classified as Prostaglandin Antagonists.)|Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)

8.13 Use Classification: Polyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]

9. Computational chemical data

Molecular Weight: 270.23700g/mol
Molecular Formula: C₁₅H₁₀O₅
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 270.05282342
Monoisotopic Mass: 270.05282342
Complexity: 413
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 3
Hydrogen Bond Acceptor Count: 5
Topological Polar Surface Area: 87
Heavy Atom Count: 20
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBwOAAAAAAAAAAAAAAAAAAAAAAAAAAwYIAAAAAAAACBQAAAGgAACAAADASAmAAwBoAABgCIAqBSAAACCAAkIAAIiAEGiMgNJzaGNRqCeWGl4BUJuQfK7LzOIQABCAAIQABCAAIQABCAAAAAAAAAAA==

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