Dihydroberberine
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Basic information
- CAS
120834-89-1- Standard SMILES
COc1ccc2c(c1OC)CN1CCc3cc4c(cc3C1=C2)OCO4- InChIKey
FZAGOOYMTPGPGF-UHFFFAOYSA-N- Molecular formula
- C20H19NO4
- Average molar mass
- 337.4 g/mol
- Monoisotopic mass
- 337.13140809
Names & identifiers
- Preferred name
- Dihydroberberine
- IUPAC
- 16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(21),2,4(8),9,15(20),16,18-heptaene
- English name
- dihydroberberine
- Molecular formula
- C20H19NO4
- Molecular weight
- 337.37
Names & synonyms
Dihydroberberine483-15-8Dihydroumbellatine7,8-Dihydroberberine16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(21),2,4(8),9,15(20),16,18-heptaeneDTXSID7019747616,17-dimethoxy-5,7-dioxa-13-azapentacyclo(11.8.0.02,10.04,8.015,20)henicosa-1(21),2,4(8),9,15(20),16,18-heptaeneRefChem:587701DTXCID80119967DihydroberbineLambertine9,10-Dimethoxy-6,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline
Show more names
Nsc331264DihyddroberberineDihydroberberine-RMdihydroberberine CASBerberine Dihydro ImpurityDihydroberberine (Standard)
lambertinDihydroberberine/dihydroumbellatine3btiBerberine, dihydro-MFCD000223129,10-Dimethoxy-2,3-(methylenedioxy)-13,13a-didehydroberbineBERBINE, 13,13a-DIDEHYDRO-9,10-DIMETHOXY-2,3-(METHYLENEDIOXY)-6H-Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizine, 5,8-dihydro-9,10-dimethoxy-
Database identifiers
- CAS
120834-89-1、483-15-8- PubChem CID
- 10217
- DTXSID
DTXSID70197476- ChEMBL
CHEMBL11848- ChEBI
CHEBI:192073- EC Number
- 683-111-2
- Nikkaji
- J126.057J
Properties
Computed structural propertiesFilling in
- XLogP
- 3.5
- Topological polar surface area
- 40.2 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 538
Experimental & physicochemical properties
Melting Point163 - 164 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 223 · 223-224℃ (dec.)
- Boiling point
- 557.8 · 557.8±50.0 °C(Predicted)
- Density
- 1.37 · 1.37±0.1 g/cm3 (20 ºC 760 Torr)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Soluble in DMSO
- pka
- 3.08 · 3.08±0.20(Predicted)
- form
- crystals
- color
- Yellow
- Water Solubility
- 57.46 mg/l · Soluble to 57.46 mg/l in water
- InChI
- InChI=1S/C20H19NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,7-9H,5-6,10-11H2,1-2H3
- InChIKey
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
Danger
H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.；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. For more detailed information, please visit ECHA C&L website.
Hazard information
Hazard Classes and CategoriesAcute Tox. 2 (100%)
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS02
- Hazard statements
- H302-H315-H319-H226
- Precautionary statements
- P501-P270-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P337+P313-P305+P351+P338-P362+P364-P303+P361+P353-P332+P313-P301+P312+P330-P403+P235
Chemistry & industry
Pharmacology
Cellular LocationsMembrane
Applications
DescriptionDihydroberberine: a natural derivative of BerberineDihydroberberine (DHB) is emerging as a popular supplement for its enhanced bioavailability and therapeutic efficacy compared to its precursor, Berberine. Berberine, a natural compound, has been widely used for its antimicrobial and anti-inflammatory properties. It has also shown promise in improving glucose and lipid metabolism, supporting cardiovascular health, and offering neuroprotective effects.
UsesDihydroberberine is a derivative Berberine (B318150), an isoqinoline alkaloid shown to have a chemopreventive property against colon tumor formation by inhibiting the enzyme cyclooxygenase-2 (cox-2) which is abundantly expressed in colon cancer cells.
Additional notes
DefinitionChEBI: Lambertine is an alkaloid.
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