Citrostadienol
Chemical compound
From Wikipedia, the free encyclopedia
Citrostadienol is a naturally occurring phytosterol with the chemical formula C30H50O, obtained from citrus species. As a 4-desmethylsterol[2][3], it is a biosynthetic precursor in the plant sterol pathway and has attracted scientific interest for its potential biological activities, particularly its antimicrobial properties.[4] The compound also belongs to the sterol class of steroids.[5]
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| Names | |
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| IUPAC name
(3S,4S,5S,9R,10S,13R,14R,17R)-4,10,13-trimethyl-17-[(Z,2R)-5-propan-2-ylhept-5-en-2-yl]-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| 3222151 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C30H50O | |
| Molar mass | 426.729 g·mol−1 |
| Appearance | powder |
| Density | 0.96 g/cm3[1] |
| Melting point | 161.6 |
| poorly soluble | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Structure
The сitrostadienol structure is characterized by a double bond between the C-7 and C-8 positions (a Δ7 bond) in the sterol nucleus, classifying it as a Δ7-sterol. This fact distinguishes it from more common plant sterols like β-sitosterol or stigmasterol, which are typically Δ5-sterols.[6]
Natural occurrence
The compound is found primarily in the Rutaceae family, especially citrus species, and in grains like oats (genus Avena). The compound is also present in the fruits of Schizandra chinensis.[7]
Synthesis
In plants, citrostadienol is synthesized via the acetate-mevalonate pathway.[8] It is an intermediate in the biosynthesis of other sterols, formed from epoxysqualene and further metabolized. Its accumulation varies among plant species and tissues.
Physical properties
The compound forms powder. Poorly soluble in water, but soluble in chloroform, dichloromethane, ethyl acetate, DMSO, acetone, etc.[9]
Uses
Ongoing scientific investigations are exploring its potential as a natural antimicrobial for diverse uses.[10] These include food preservation, where it could combat spoilage organisms to prolong product shelf life, and pharmaceuticals, especially in topical formulations for bacterial or fungal infections. Studies are also evaluating its effectiveness and safety to determine its suitability for inclusion in antimicrobial consumer products.[11][12]