| Identification | Back Directory | [Name]
dihydroberberine | [CAS]
483-15-8 | [Synonyms]
Nsc331264
Dihydroberbine
dihydroberberine
DihydrouMbellatine
Berberine Dihydro Impurity
Dihydroberberine/Dihydroumbellatine
9,10-Dimethoxy-2,3-(methylenedioxy)-13,13a-didehydrob
9,10-Dimethoxy-2,3-(methylenedioxy)-13,13a-didehydroberbine
5,8-Dihydro-9,10-dimethoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine
6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine, 5,8-dihydro-9,10-dimethoxy-
9,10-DiMethoxy-6,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline | [Molecular Formula]
C20H19NO4 | [MOL File]
483-15-8.mol | [Molecular Weight]
337.37 |
| Chemical Properties | Back Directory | [Melting point ]
223-224℃ (dec.) | [Boiling point ]
557.8±50.0 °C(Predicted) | [density ]
1.37±0.1 g/cm3 (20 ºC 760 Torr) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Soluble in DMSO | [form ]
crystals | [pka]
3.08±0.20(Predicted) | [color ]
Yellow | [Water Solubility ]
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]
FZAGOOYMTPGPGF-UHFFFAOYSA-N | [SMILES]
C12C=C3C(=CC=1CCN1C2=CC2=CC=C(OC)C(OC)=C2C1)OCO3 |
| Hazard Information | Back Directory | [Description]
Dihydroberberine: a natural derivative of Berberine
Dihydroberberine (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.
| [Chemical Properties]
Yellow crystals, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from Berberis. | [Uses]
Dihydroberberine 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. | [Definition]
ChEBI: Lambertine is an alkaloid. | [Synthesis]
Briefly, 5% sodium hydroxide solution (27?mL) containing sodium borohydride (2.7?g) was added to a stirred solution of berberine chloride (11.06?g) and potash (13.1?g) in methanol (150?mL) dropwise. After stirring the reaction mixture at ambient temperature for 3?h, the precipitation was filtered and scrubbed with 30% ethanol (200?mL) followed by 80% ethanol (100?mL). The green–brown crystals were filtered and dried at 30?°C and were then collected to afford 9.4?g (yield: 85%) Dihydroberberine[1].
| [in vivo]
Dihydroberberine (250 mg/kg; intragastric gavage, once every other day for 14 days) effectively inhibits tumor growth and proliferation in the mouse NCI-H460 xenograft model and exhibits synergistic with Sunitini[2].
| [IC 50]
HSP90 | [storage]
Store at -20°C,sealed storage, away from moisture and light | [References]
[1] Lihua Tan . “Dihydroberberine, a hydrogenated derivative of berberine firstly identified in Phellodendri Chinese Cortex, exerts anti-inflammatory effect via dual modulation of NF-κB and MAPK signaling pathways.” International immunopharmacology 75 (2019): Article 105802.
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