dihydroberberine Property

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

pka

3.08±0.20(Predicted)

form 

crystals

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 and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H226Flammable liquid and vapour

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

P242Use only non-sparking tools.

P243Take precautionary measures against static discharge.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P370+P378In case of fire: Use … for extinction.

P403+P235Store in a well-ventilated place. Keep cool.

P501Dispose of contents/container to..…

dihydroberberine Chemical Properties,Usage,Production

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.

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].

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.