Алиссин

Description

Alissin is a plant-derived isothiocyanate, a sulfonyl analogue of sulforaphane. CAS number 646-23-1, English name Alyssin, other designations: 5-methylsulfinylpentyl isothiocyanate, pentane-1-isothiocyanato-5-(methylsulfinyl). Formula C7H13NOS2.

Basic Attributes

• CAS No.: 646-23-1
• Chemical formula: C7H13NOS2
• Molecular weight: 191.31
• Exact weight: 191.31
• HS code: 293090909090
• PSA specifications: 80.7
• XLogP3: 2.50370

Physico-chemical characteristics

• Density: 1.14 g/cm3
• Boiling point: 130–135 °C at 0.02 Torr pressure
• Flash point: 181.4 °C
• Refractive index: 1.558

Substance class and biological activity

Alissin belongs to isothiocyanates - a class of sulfur-containing secondary metabolites of plants of the cruciferous family, formed during the enzymatic hydrolysis of glucosinolates under the action of the enzyme myrosinase; In an intact plant, glucosinolate and myrosinase are separated, and the reaction is triggered by tissue damage. Alyssin is a homologue of sulforaphane and is related to erucin—both compounds from the same isothiocyanate family are being studied for their antioxidant, anti-inflammatory, and chemopreventive properties. It is known that alissin reduces the enzymatic metabolism of polycyclic aromatic hydrocarbons, thereby reducing the carcinogenic risk and exhibiting a potential chemopreventive effect, and also induces enzymes of the second phase of detoxification and increases the level of the transcription factor Nrf2 in adenocarcinoma cells. These properties make the substance an object of research in the field of nutritional biochemistry and preventive oncology, where alissin is used as a reference standard in the study of glucosinolate metabolism and the comparative activity of plant isothiocyanates.

The molecular formula C7H13NOS2 reflects the two sulfur functional groups in the structure: an isothiocyanate (–N=C=S) group at the end of the alkyl chain and a methylsulfinyl (–S(=O)CH3) group toward the other end. Along the length of the carbon chain, alyssin is one methylene unit longer than sulforaphane, which determines the status of a structural homologue. The reactive isothiocyanate group is capable of forming covalent bonds with the thiol groups of target proteins; it is this mechanism that underlies the induction of phase two detoxification enzymes in most plant isothiocyanates.

The compound is isolated and studied along with other representatives of the same biochemical series - sulforaphane, erucin, ibervirine - comparing the length of the alkyl chain and the position of the sulfinyl group with the severity of the antioxidant and chemopreventive effect. Such comparative series help to establish which structural features of a molecule are important for biological activity.

Storage and handling

Isothiocyanates are generally reactive and volatile, with a pungent odor; It is recommended to store in an airtight container, in a cool place, away from sources of open flame, taking into account the indicated flash point of 181.4 °C, using respiratory protection when working with the concentrate. Avoid prolonged contact with skin and inhalation of vapors due to the irritant effects of isothiocyanates. The reactive isothiocyanate group interacts with the thiol groups of proteins, so it is recommended to use gloves that are resistant to organic solvents when working.