Глицирин

Identification

Glycyrin (CAS 66056-18-6) is a natural coumarin of licorice root (Glycyrrhiza uralensis). The chemical formula is C22H22O6 - not to be confused with glycerin (propanetriol), these are different substances with a similar name and different chemical nature. The systematic name is 3-(2,4-dihydroxyphenyl)-5,7-dimethoxy-6-(3-methyl-2-buten-1-yl)-2H-1-benzopyran-2-one.

Physico-chemical characteristics

• Molecular Weight: 382.412
• Exact weight: 382.41
• UNII: 994BQ9M3AV
• DSSTox ID: DTXSID50216255
• PSA Specifications: 85.2
• XLogP3: 4.7
• Density (predicted): 1.275±0.06 g/cm3
• Melting point: 209–211 °C

There are no other physical parameters (boiling, flash, refractive index, solubility) in the dump - the data is not made up. XLogP3 4.7 indicates a pronounced lipophilicity of the molecule due to the prenyl (3-methyl-2-butenyl) substituent and two methoxy groups on an overall moderately polar benzopyran framework (PSA 85.2).

Substance class and biological activity

Glycyrin belongs to the licorice root coumarins, the same group as glycirol and glycicoumarin. Of these three natural coumarins, glycyrin exhibits the most pronounced anti-inflammatory activity, realized through suppression of the activation of proinflammatory cytokines TNF-α, IL-6 and IL-1β. A study of the metabolism of glycirin and glycirol showed their low oral bioavailability with high metabolic stability - the compounds are poorly absorbed in the intestine, but are resistant to further destruction by enzymes, which prolongs the period of their presence in the body. Licorice root, from which glycyrin is isolated, is traditionally valued primarily for the triterpene saponin glycyrrhizin, but the coumarin fraction makes its own independent contribution to the overall pharmacological profile of the plant material.

Scope of application

• reference standard for phytochemical control of licorice extracts and preparations
• object of pharmacological research on the anti-inflammatory activity of licorice coumarins
• material from comparative pharmacokinetic studies in the series of Glycyrrhiza coumarins
• marker of raw material authenticity during pharmacognostic testing

Storage and transportation

No data found on transport codes, hazard class or GHS phrases. Crystalline powder with a melting point of 209–211 °C is recommended to be stored in a dry, dark and cool place, in an airtight container, and to wear gloves when weighing to avoid inhaling dust.

Place in phytochemistry of licorice

In addition to the triterpene saponin glycyrrhizin, to which licorice owes its fame, the plant contains rich flavonoid and coumarin fractions. Glycyrin, glycirol and glycicoumarin are three structurally related coumarins of this fraction, differing in the position of methoxy groups and hydroxyl substituents on the common benzopyran skeleton, which determines subtle differences in their biological activity with general structural similarity. The plant Glycyrrhiza uralensis and the related species Glycyrrhiza glabra are the main botanical sources of licorice root, used in both traditional and modern herbal medicine around the world.