Tirucallol

Tirucallol

Skeletal formula
Names
Preferred IUPAC name (3β)-Dammara-7,24-dien-3-ol
Identifiers
CAS Number	514-46-5  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:175463
ChemSpider	91501
PubChem CID	101257
CompTox Dashboard (EPA)	DTXSID001317294
InChI InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25-,26-,28+,29-,30+/m0/s1 Key: CAHGCLMLTWQZNJ-HGKXYCPESA-N
SMILES C[C@@H](CCC=C(C)C)[C@@H]1CC[C@]2([C@]1(CCC3=C2CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)C)C
Properties
Chemical formula	C30H50O
Molar mass	426.72 g/mol
Appearance	White to off-white solid
Density	~1.0 g/cm3 (estimated)
Solubility in water	Practically insoluble in water; soluble in ethanol, DMSO
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Not extensively studied; handle as potentially bioactive
Flash point	Not applicable
Autoignition temperature	Not applicable
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N (what is  YN ?) Infobox references

Tirucallol is a naturally occurring tetracyclic triterpenoid alcohol found in various plant species, notably in the latex of Euphorbia lactea and the resin of Pistacia lentiscus (mastic tree). It is structurally related to other triterpenes and has been studied for its potential anti-inflammatory and antioxidant properties. ^[1]

Occurrence

Tirucallol has been isolated from the latex of Euphorbia lactea and from the resin of Pistacia lentiscus , commonly known as mastic gum. These natural sources have been traditionally used for their medicinal properties, and the presence of tirucallol contributes to their bioactivity. ^{[2] [3]}

Structure and biological activity

Tirucallol possesses a dammarane-type skeleton with a hydroxyl group at the 3β-position, classifying it as a tetracyclic triterpenoid alcohol. It is biosynthesized in plants via the mevalonate pathway, which leads to the formation of squalene and subsequent cyclization to various triterpenes. ^[1]

Research indicates that tirucallol exhibits several biological activities:

• Anti-inflammatory properties: Topical application of tirucallol has been shown to suppress ear edema in mouse models and inhibit nitrite production in lipopolysaccharide-stimulated macrophages, suggesting its potential as an anti-inflammatory agent. ^[2]
• Cardioprotective effects: Tirucallol has been found to inhibit the expression of adhesion molecules (VCAM-1 and ICAM-1) in tumor necrosis factor-alpha (TNF-α) stimulated human aortic endothelial cells, indicating a role in preventing endothelial dysfunction and atherosclerosis. ^[3]

Potential applications

Due to its natural origin and bioactive potential, tirucallol is particularly of interest in:

• Pharmaceutical research: Its anti-inflammatory and cardioprotective properties make it a candidate for drug development targeting related conditions.
• Nutraceutical development: As a component of mastic gum, it may contribute to the health benefits attributed to this traditional remedy.
• Cosmetic formulations: The compound's bioactivity may be beneficial in skincare products aimed at reducing inflammation and oxidative damage.

References

1. "Tirucallol". PubChem. Retrieved 2025-05-23.
2. Fernandez-Arche, A. (2010). "Topical anti-inflammatory effect of tirucallol, a triterpene isolated from Euphorbia lactea latex". Phytomedicine. 17 (2): 146–148. doi:10.1016/j.phymed.2009.05.009. PMID   19577446.
3. Loizou, S. (2009). "Chios Mastic Gum Extract and Isolated Phytosterol Tirucallol Exhibit Anti-Inflammatory Activity in Human Aortic Endothelial Cells". Experimental Biology and Medicine. 234 (5): 553–561. doi:10.3181/0811-RM-338. PMID   19234052.