Basic information
- CAS
206752-33-2- Standard SMILES
O=C(O)[C@H]1O[C@@H](Oc2cc3oc(-c4ccccc4)cc(=O)c3c(O)c2O)[C@H](O)[C@@H](O)[C@@H]1O- InChIKey
IKIIZLYTISPENI-ZFORQUDYSA-N- Molecular formula
- C21H18O11
- Average molar mass
- 446.4 g/mol
- Monoisotopic mass
- 446.08491139
Overview
Baicalin is the glycosyloxyflavone which is the 7-O-glucuronide of baicalein. It is an active ingredient of Chinese herbal medicine Scutellaria baicalensis. It has a role as an antiatherosclerotic agent, an anticoronaviral agent, an EC 2.7.7.48 (RNA-directed RNA polymerase) inhibitor, a ferroptosis inhibitor, an antioxidant, an antibacterial agent, a non-steroidal anti-inflammatory drug, an antineoplastic agent, a prodrug, a neuroprotective agent, an EC 3.4.21.26 (prolyl oligopeptidase) inhibitor, a plant metabolite and a cardioprotective agent. It is a glucosiduronic acid, a dihydroxyflavone, a glycosyloxyflavone and a monosaccharide derivative. It is functionally related to a baicalein. It is a conjugate acid of a baicalin(1-).
Names & identifiers
- Preferred name
- Baicalin
- IUPAC
- (2S,3S,4S,5R,6S)-6-(5,6-dihydroxy-4-oxo-2-phenylchromen-7-yl)oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
- English name
- BAICALIN HYDRATE
- Molecular formula
- C21H18O11.H2O
- Molecular weight
- 464.377
Names & synonyms
Baicalin21967-41-9Baicalein 7-O-glucuronideBaicalein 7-glucuronide7-D-Glucuronic acid-5,6-dihydroxyflavone5,6-dihydroxy-4-oxo-2-phenyl-4H-1-benzopyran-7-yl beta-D-glucopyranosiduronic acidCHEBI:2981347Q89U4M55,6-dihydroxy-4-oxo-2-phenyl-4H-chromen-7-yl beta-D-glucopyranosiduronic acidDTXSID701346569(2S,3S,4S,5R,6S)-6-(5,6-dihydroxy-4-oxo-2-phenylchromen-7-yl)oxy-3,4,5-trihydroxyoxane-2-carboxylic acid7-D-glucuronic acid-5,6-dihydroxy-flavone
Show more names
baicalein 7-β-d-glucopyranosiduronate5,6-Dihydroxy-4-oxo-2-phenyl-4H-1-benzopyran-7-yl beta-D-glucopyranosiduronic acid hydrate
beta-D-Glucopyranosiduronic acid, 5,6-dihydroxy-4-oxo-2-phenyl-4H-1-benzopyran-7-yl5,6,7-trihydroxyflavone-7-O-beta-D-glucuronateRefChem:5580DTXCID901775235633-784-3BaicalosideMFCD00134418(2S,3S,4S,5R,6S)-6-((5,6-dihydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid
Properties
Computed structural properties
- XLogP
- 1.1
- Topological polar surface area
- 183 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 11
- Rotatable bonds
- 4
- Heavy atoms
- 32
- Formal charge
- 0
- Complexity
- 748
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]
Physicochemical properties
- Melting point
- 231 · 231-233 °C(lit.)
- form
- powder
- optical activity
- 23 · [α]23/D 120°, c = 1 in 50% pyridine
- InChIKey
- WLEKZZMZTPAGDD-ZSESPEEFSA-N
- SMILES
- O.O[C@@H]1[C@@H](O)[C@@H](O[C@@H]([C@H]1O)C(O)=O)Oc2cc3OC(=CC(=O)c3c(O)c2O)c4ccccc4
- UNSPSC Code
- 12352005 · 12352005
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P305+P351+P338
- target organs
- Respiratory system
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (93.6%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 47 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
Hazard information
Regulatory Information
(2S,3S,4S,5R,6S)-6-(5,6-dihydroxy-4-oxo-2-phenyl-chromen-7-yl)oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and Categories
Skin Irrit. 2 (93.6%)
Skin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- hs_code
- 29329985
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
Mechanism of ActionA 2025 review notes anti-inflammatory, antioxidant, antitumor, antiviral, and antimicrobial effects through modulation of key pathways (NF-κB, Nrf2, TLR4/MyD88, and PI3K/AKT).
MeSH Pharmacological Classification
Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Drugs that are used to treat asthma.
Absorption, Distribution and Excretion
A 2025 systematic review notes that while Baicalin has poor oral bioavailability due to its low water solubility and limited membrane permeability, Baicalein exhibits superior lipophilicity and permeability. Baicalin is hydrolyzed to Baicalein by gut microbiota and enzymes. UDP-glucuronosyltransferases in enterocytes in the intestines and in the liver can convert Baicalein back to Baicalin. Thus, conversion of Bacalin to Baicalein facilitates systemic uptake while re-glucuronidation of Bacalein to Bacalin potentially prolongs the therapeutic effects.
Applications
UsesThe flavonoid component of Nepalese and Sino-Japanese crude drugs.
Suppliers15 total
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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