116-26-7 Usage
Chemical Properties
2,6,6-Trimethylcyclohexa-1,3-dienyl methanal has a characteristic saffron-like odor and taste.
Occurrence
Occurring naturally as a glucoside (picrocrocin) in saffron. Also reported found in grapefruit juice, saffron,
black tea, green tea, microbial fermented tea, Bourbon vanilla, lemon balm, grapefruit juice, maté and sweet grass oil.
Uses
Safranal, is isolated from Saffron, and is primarily responsible for the aroma of saffron. It has also been shown to have anticonvulsant properties, acting as agonist at GABAA receptors. It is also possessing anticancer and antidepressant properties.
Definition
ChEBI: A monoterpenoid formally derived from beta-cyclocitral by dehydrogenation.
Preparation
By acid hydrolysis of picrocrocin, the bitter principle in saffron; by catalytic dehydrogenation of β-cyclocitral or
α-cyclogeranic acid with selenium dioxide.
Taste threshold values
Taste characteristics at 1 ppm: woody, medicinal, spicy and camphoraceous with a fruity and herbal nuance.
Flammability and Explosibility
Notclassified
Check Digit Verification of cas no
The CAS Registry Mumber 116-26-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 6 respectively; the second part has 2 digits, 2 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 116-26:
(5*1)+(4*1)+(3*6)+(2*2)+(1*6)=37
37 % 10 = 7
So 116-26-7 is a valid CAS Registry Number.
InChI:InChI=1/C10H14O/c1-8-5-4-6-10(2,3)9(8)7-11/h4-5,7H,6H2,1-3H3
116-26-7Relevant articles and documents
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Kametani,T. et al.
, p. 1128 - 1129 (1979)
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γ-Pyronene, a synthon derived from saffron and intermediary precursor of synthesis of forskolin and strigol
Boulin,Arreguy-San Miguel,Delmond
, p. 2753 - 2762 (2007/10/03)
γ-Pyronene, a terpenic synthon available from myrcene, is an excellent raw material for the preparation of numerous intermediates used in the synthesis of perfumes, retinoids and biological derivatives such as forskolin or strigol.
The chemistry of thujone. XVI. Versatile and efficient routes to safronitrile, β-cyclogeranonitrile, β-cyclocitral, damascones, and their analogues
Kutney, James P.,Gunning, Philip J.,Clewley, Robin G.,Somerville, John,Rettig, Steven J.
, p. 2094 - 2114 (2007/10/02)
Thujone, a waste by-product of the Canadian forest industry, has been utilized as a starting material to develop a versatile synthetic route to the damascones (rose oil ketones) and related analogues.The synthetic sequence provides a route to β-cyclocitral (45), the latter having been previously converted to β-damascone (2).In addition, thujone-drived intermediates are converted to β-damascenone (48) and to intermediates that can be utilized for the preparation of damascone analogues.In conjunction with the above, an efficient route to safronitrile (42), β-cyclogeranonitrile (43), and β-cyclocitral (45) from 2,6-dimethylcyclohexanone has been developed.In summary, these studies afford an attractive versatile route to these important perfumery materials.
