Geranyl acetone, also known as 6,10-dimethyl-5,9-undecadien-2-one; 6,10-dimethyl-5,9- undecadiene-2-one, dihydropseudoionone, α, β-dihydropseudoionone, is a derivative of linalool. CAS Registry Number: 689-67-8. Molecular formula: C13H22O, molecular weight: 194.3132. The chemical structure is:
Geranyl acetone is a light yellow to colorless, transparent and oily liquid with an aroma of magnolia. Its boiling point is 250°C (101.3 kPa), and the flash point is 101°C. The density is 0.8729 g.cm–3 and the refractive index is 1.4674 at 20°C. Geranyl acetone has a (Z)-isomer, neryl acetone or (Z)-geranyl acetone.
Geranyl acetone is a fragrance and flavor substance, which is widely used in foods, beverages, cosmetics, household cleaners and detergents. It can be used to formulate a variety of flavors such as apple, banana and citrus essence. When used in the preparation of citrus essence, it can effectively prevent the bitter and astringent taste of real citrus. Geranyl acetone can be used in both rose-flavored flavors as an auxiliary flavor in non-flora. The combination of geranyl acetone and lavender and fruity is very effective, which can play the role of refreshing and natural aroma and make the floral fragrance more mellow. In addition, geranyl acetone is also used in the cigarette industry to enhance the coordination of smoke aroma.
Geranyl acetone is a key intermediate for the synthesis of dehydronerolidol and farnesol and is also a key intermediate in the production of isophytol. Isophytol is an important side chain of synthetic vitamin E, and an increase in the demand for vitamin E is bound to expand the production of geranyl acetone.
Geranyl-geranyl acetone (GGA), a new acyclic polyisoprenoid, anti-ulcer drug appears to exert its beneficial effect by stimulating bicarbonate secretion from the stomach and pancreas. Its efficacy in Stimulating pancreatic bicarbonate is particularly striking, and this study was designed to examine the mechanism for this action. Since it is structurally similar to the side chain of the prostaglandin molecule, its ability to stimulate bicarbonate secretion could be a direct one. On the other hand, the magnitude of pancreatic bicarbonate response (about 50% of maximal response to secretin) suggests it might act by releasing secretin.
Two types of experiments were performed in dogs with pancreatic fistulas: first, secretagogue interactions were examined by studying the effect of intraduodenal GGA (8 mg/kg) or its carrier (control) on the dose response curves to exogenous secretin and cholecystokinin octapeptide (CCK-8); second, the effect of graded doses of intraduodenal GGA on pancreatic bicarbonate and plasma secretin-like immunoreactivity (SLI) responses was tested directly. Pancreatic bicarbonate responses (micromoles per 30 min) were to secretin doses of 32, 125, and 500 ng/kg/h. Without and with GGA, responses were 74 ± 27, 952 ± 215, and 2,000 ± 425 and 599 ± 110, 1,624 ± 472, and 2,129 ± 398 ng/kg/h, respectively. Similarly, the bicarbonate responses to CCK-8 were augmented. Basal plasma SLI was 1.5* 0.6 pM/ml. Peak plasma SLI in response to 2, 4, and 8 mg of GGA intraduodenally were6.8 ± 0.7, 8.9 ± 3.1, and 19.6 ± 2.7 pM/ml, respectively. It is concluded that GGA is a potent stimulant of pancreatic bicarbonate secretion, and this action appears to be mediated by the release of duodenal secretin.
References:
[1] H. DEBAS. Geranyl‐Geranyl Acetone: A Novel Stimulant of Secretin Release in the Dog[J]. Pancreas, 1990. DOI:10.1097/00006676-199009000-00010.
