Masticadienonic acid

Masticadienonic acid
	Skeletal formula
Names
	Preferred IUPAC name (E)-2-methyl-6-(4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl)hept-2-enoic acid
	Other names (24Z)-3-oxolanosta-7,24-dien-26-oic acid
Identifiers
CAS Number	514-49-8;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:172023;
ChemSpider	9514955;
PubChem CID	5951616;
CompTox Dashboard (EPA)	DTXSID101315065 ;
	InChI InChI=1S/C30H46O3/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/h10-11,19,21-22,24H,8-9,12-18H2,1-7H3,(H,32,33)/b20-10+ Key: VOYZLKWKVLYJHD-KEBDBYFISA-N; InChI=1S/C30H46O3/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/h10-11,19,21-22,24H,8-9,12-18H2,1-7H3,(H,32,33)/b20-10-/t19-,21-,22-,24-,28+,29-,30+/m0/s1 Key: VOYZLKWKVLYJHD-UZEUFRBSSA-N;
	SMILES CC(CC/C=C(\C)/C(=O)O)C1CCC2(C1(CCC3C2=CCC4C3(CCC(=O)C4(C)C)C)C)C; C/C(=C/CC[C@H](C)[C@@H]1CC[C@]2(C)C3=CC[C@H]4C(C)(C)C(=O)CC[C@]4(C)[C@H]3CC[C@@]12C)C(=O)O;
Properties
Chemical formula	C30H46O3
Molar mass	454.69 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

Masticadienonic acid is a triterpenoid compound – a natural product – derived from the resin of Pistacia lentiscus (the mastic tree), which belongs to the family of tirucallane-type tetracyclic triterpenoids based on its structural characteristics and biosynthetic origin, and has shown biological activity in scientific studies, such as anti-inflammatory properties.^[1]^[2]

Occurrence

Masticadienonic acid is one of the major constituents of mastic gum, which is a natural resin exuded from the bark of Pistacia lentiscus, a plant native to the Mediterranean region,^[2] especially on the Greek island of Chios. It is typically accompanied by masticadienolic acid and other triterpenoid compounds.

Structure and biological activity

This compound has a lanostane skeleton with a carboxylic acid group and a conjugated enone system. It is biosynthesized in the plant through the mevalonate pathway, which is common for all triterpenes and steroids.^[1]

Studies suggest that masticadienonic acid exhibits an extensive variety of biological activities:

It shows anti-inflammatory properties through modulation of pro-inflammatory pathways such as NF-κB.^[2]
It has antitumor effects in certain cancer models, including prostate cancer, through induction of apoptosis.^[2]
It can inhibit enzymes related to steroid metabolism, such as 11β-hydroxysteroid dehydrogenase, although this effect is still under further investigation.^[1]

Applications

Because of its natural origin and bioactive potential, masticadienonic acid is of high interest in:

Nutraceutical development
Traditional herbal medicine research
Drug discovery as a scaffold for semi-synthetic derivatives

References

^ ^a ^b ^c "Masticadienonic acid". PubChem. Retrieved 2025-05-23.
^ ^a ^b ^c ^d 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)

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

[Paraschos2007-2] 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]

[2]