Сугиол

Description

Sugiol is a natural diterpenoid of the abietane series with a phenolic hydroxyl group and a keto group in ring C. Full nomenclature name: (4aS,10aS)-2,3,4,4a,10,10a-hexahydro-6-hydroxy-1,1,4a-trimethyl-7-(1-methylethyl)-9(1H)-phenanthrone; in terpene nomenclature - 12-hydroxy-13-isopropylpodocarpa-8,11,13-trien-7-one. The compound is isolated from the bark of Cryptomeria japonica (sugi), hence the name, and is also found in other conifers and in plants of the genus Salvia. Structurally close to ferruginol, the same abietane skeleton without a keto group at position 7. The synonym 10-deoxantoperol reflects the relationship with xanthoperol.

Identification

• CAS No: 511-05-7
• Chemical formula: C20H28O2
• Molecular weight: 300.442; exact weight: 300.44
• NSC Number: 122421
• Class of compounds: terpenes, abietane diterpenoids
• Stereochemistry: configuration (4aS,10aS), the designation (4aS-trans) is found in the literature; optically active form - (+)-sugiol

Physico-chemical properties

• Density: 1.0 ± 0.1 g/cm³
• Melting point: 290–292 °C (with decomposition)
• Boiling point: 185–205 °C at 0.1 Torr pressure
• Flash point: 186.4 ± 21.3 °C
• Refractive index: 1.539
• Solubility in water: 0.208 mg/l at 25 °C (estimated)
• PSA specifications: 37.3
• XLogP3: 6.77

The combination of XLogP3 6.77 and polar surface 37.3 describes a strongly lipophilic molecule with two oxygen functions. Solubility in water at 0.208 mg/l is practically zero; working solutions are prepared in dimethyl sulfoxide, ethanol, methanol, chloroform. Boiling is indicated at high vacuum (0.1 Torr) - at atmospheric pressure the substance decomposes earlier, as evidenced by the nature of melting at 290–292 °C.

Origin and receipt

The main source is the bark of Cryptomeria japonica. Abietanoid diterpenoids of this species have been studied in detail: both known compounds, including sugiol, and new representatives of the series, including dimeric abietanoid peroxides, have been isolated from the bark. Isolation is carried out by extraction of plant materials with an organic solvent followed by chromatographic purification; The purity of the commercial product is confirmed by HPLC, NMR and mass spectrometry.

Scope of application

• Reference standard for phytochemical analysis: identification and quantification of abietane diterpenoids in extracts of conifers and plants of the genus Salvia by HPLC and GC-MS.
• Object of scientific research. Sugiol is one of the main components of active extracts of sugi bark, for which growth inhibitory activity has been noted. Diterpenes from Cryptomeria japonica have been studied as inhibitors of androgen receptor transcriptional activity in prostate cancer cells. The therapeutic effects of sugiol and the molecular pathways involved have been the subject of a separate review in the literature.
• The starting compound for the semisynthesis of abietane derivatives: the phenolic hydroxyl and the keto group provide two independent points of modification.

Safety Information

The GHS classification, hazard statements, precautionary statements and transport data for this substance are not available on the original card. The product is supplied in quantities specific to analytical standards and research work and is intended for laboratory use. Handling - according to the general rules for working with organic substances of unknown toxicity: gloves, safety glasses, lab coat, all operations with powder under a hood.

Storage and handling

Standard conditions for natural phenolic compounds: sealed containers, protection from light and oxygen, storage at low temperatures. The phenolic group oxidizes in light and air, so dark glass and an inert atmosphere are preferred. Solutions in organic solvents are stored frozen and protected from repeated freeze-thaw cycles. The specific regime is specified using the batch passport from the supplier.