Masticadienolic acid

Masticadienolic acid
	Skeletal formula
Names
	Preferred IUPAC name (Z,6S)-6-[(3S,5R,9R,10R,13S,14S,17S)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylhept-2-enoic acid
Identifiers
CAS Number	472-30-0;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL5266227;
ChemSpider	28425558;
PubChem CID	102004474;
	InChI InChI=1S/C30H48O3/c1-19(9-8-10-20(2)26(32)33)21-13-17-30(7)23-11-12-24-27(3,4)25(31)15-16-28(24,5)22(23)14-18-29(21,30)6/h10-11,19,21-22,24-25,31H,8-9,12-18H2,1-7H3,(H,32,33)/b20-10-/t19-,21-,22-,24-,25-,28+,29-,30+/m0/s1 Key: UILQHUKSFUOOLH-MCGHDPRASA-N;
	SMILES C[C@@H](CC/C=C(/C)\C(=O)O)[C@@H]1CC[C@]2([C@]1(CC[C@H]3C2=CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)C)C;
Properties
Chemical formula	C30H48O3
Molar mass	456.71 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). (what is ?) Infobox references

Masticadienolic acid is a naturally occurring terpenoid compound found in the resin of the mastic tree (Pistacia lentiscus), particularly in the variety cultivated on the Greek island of Chios. Chemically, it is a tirucallane-type tetracyclic triterpenoid based on its structural characteristics and biosynthetic origin. It is structurally related strongly to masticadienonic acid, differing by the presence of a hydroxyl group, which may influence its biological activity.^[1]

Occurrence

Masticadienolic acid is one of the major constituents of mastic gum, a natural resin exuded from the bark of Pistacia lentiscus. This resin has been traditionally used for its medicinal properties and is known to contain various triterpenoids, including masticadienolic acid.^[2]

Structure and biological activity

This natural substance possesses a lanostane-type skeleton with a carboxylic acid group and a hydroxyl group, classifying it as a pentacyclic triterpenoid. It is biosynthesized in the plant via the mevalonate pathway, a common route for the formation of triterpenes and steroids.^[3]

Research indicates that masticadienolic acid exhibits several biological activities, such as:

Anti-inflammatory properties: It may modulate pro-inflammatory pathways, contributing to its traditional use in treating inflammatory conditions.^[4]
Antioxidant effects: The compound has been associated with antioxidant activity, which can protect cells from oxidative stress.^[5]
Potential anticancer activity: Preliminary studies suggest that masticadienolic acid may have cytotoxic effects on certain cancer cell lines, although further research is needed to confirm these findings.^[6]

Applications

Due to its natural origin and bioactive potential, masticadienolic acid is of interest in:

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

References

^ "Masticadienolic acid". PubChem. Retrieved 2025-05-23.
^ Tabanca, N. (2020). "Chemical Characterization and Biological Activity of the Mastic Gum Essential Oils of Pistacia lentiscus var. chia from Turkey". Molecules. 25 (9): 2136. doi:10.3390/molecules25092136. PMC 7248992. PMID 32370246.
^ "Masticadienolic acid". PubChem. Retrieved 2025-05-23.
^ Paraschos, S. (2007). "Chemical Composition and Antibacterial Activity of the Essential Oils from the Resin of Pistacia lentiscus". Journal of Agricultural and Food Chemistry. 55 (18): 7686–7690. doi:10.1021/jf070509f (inactive 1 July 2025).{{cite journal}}: CS1 maint: DOI inactive as of July 2025 (link)
^ Paraschos, S. (2007). "Chemical Composition and Antibacterial Activity of the Essential Oils from the Resin of Pistacia lentiscus". Journal of Agricultural and Food Chemistry. 55 (18): 7686–7690. doi:10.1021/jf070509f (inactive 1 July 2025).{{cite journal}}: CS1 maint: DOI inactive as of July 2025 (link)
^ Paraschos, S. (2007). "Chemical Composition and Antibacterial Activity of the Essential Oils from the Resin of Pistacia lentiscus". Journal of Agricultural and Food Chemistry. 55 (18): 7686–7690. doi:10.1021/jf070509f (inactive 1 July 2025).{{cite journal}}: CS1 maint: DOI inactive as of July 2025 (link)

[1] "Masticadienolic acid". PubChem. Retrieved 2025-05-23.

[2] Tabanca, N. (2020). "Chemical Characterization and Biological Activity of the Mastic Gum Essential Oils of Pistacia lentiscus var. chia from Turkey". Molecules. 25 (9): 2136. doi:10.3390/molecules25092136. PMC 7248992. PMID 32370246.

[3] "Masticadienolic acid". PubChem. Retrieved 2025-05-23.

[4] Paraschos, S. (2007). "Chemical Composition and Antibacterial Activity of the Essential Oils from the Resin of Pistacia lentiscus". Journal of Agricultural and Food Chemistry. 55 (18): 7686–7690. doi:10.1021/jf070509f (inactive 1 July 2025).{{cite journal}}: CS1 maint: DOI inactive as of July 2025 (link)

[5] Paraschos, S. (2007). "Chemical Composition and Antibacterial Activity of the Essential Oils from the Resin of Pistacia lentiscus". Journal of Agricultural and Food Chemistry. 55 (18): 7686–7690. doi:10.1021/jf070509f (inactive 1 July 2025).{{cite journal}}: CS1 maint: DOI inactive as of July 2025 (link)

[6] Paraschos, S. (2007). "Chemical Composition and Antibacterial Activity of the Essential Oils from the Resin of Pistacia lentiscus". Journal of Agricultural and Food Chemistry. 55 (18): 7686–7690. doi:10.1021/jf070509f (inactive 1 July 2025).{{cite journal}}: CS1 maint: DOI inactive as of July 2025 (link)

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