111-12-6 Usage
Description
METHYL 2-OCTYNOATE, also known as methyl 2-caprylate, is a fatty acid ester formed by the esterification between methanol and 2-octynoate. It is a useful flavor and fragrance agent with a strong violet-type odor and a wine-berry flavor (muscatel). It is a colorless liquid, soluble in most fixed oils and mineral oil, and slightly soluble in 70% alcohol. It has a taste threshold value of 15.0 ppm, with green, vegetative, fatty, fruity, rindy, melon, and cucumber characteristics, along with mushroom and dairy nuances.
Uses
Used in Perfumery and Flavoring:
METHYL 2-OCTYNOATE is used as a fragrance and flavoring agent for its strong violet-type odor and wine-berry flavor (muscatel), providing a unique scent and taste to various products.
Used in Cosmetics:
METHYL 2-OCTYNOATE is used as a fragrance allergen standard for the quantification of the analyte in cosmetics using chromatography techniques. It has been quantitated as a suspected allergen in cosmetic products, helping to ensure the safety and quality of these products.
Used in Chemical Synthesis:
METHYL 2-OCTYNOATE participates in nickel-catalyzed carbocyclization of 2-iodoacetophenone to yield a 2,3-disubstituted indenol, which can be used in the synthesis of various chemical compounds.
Used in Analytical Chemistry:
METHYL 2-OCTYNOATE is used in headspace-programmed temperature vaporization-fast gas chromatography-quadrupole mass spectrometry for the detection and quantification of suspected allergens in cosmetic products, aiding in the assessment of product safety and quality.
References
Barbieri, Germana, et al. "Flavor compounds of dry-cured
ham." Journal of Agricultural and Food Chemistry 40.12 (1992): 2389
-2394.
Maga, Joseph A. "Egg and egg product flavor." Journal of
Agricultural and Food Chemistry 30.1 (1982): 9-14.
Preparation
From heptaldehyde via heptyne and heptyne carboxylic acid; the acid is subsequently
Trade name
Folione? (Givaudan).
Contact allergens
This perfumed molecule belongs to the list of 26 allergens that have to be indicated by name on the ingredients list of cosmetics in the EU
Safety Profile
Moderately toxic by
ingestion and skin contact. A moderate skin
and eye irritant. A combustible liquid. When
heated to decomposition it emits acrid
smoke and irritating fumes.
Check Digit Verification of cas no
The CAS Registry Mumber 111-12-6 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 1 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 111-12:
(5*1)+(4*1)+(3*1)+(2*1)+(1*2)=16
16 % 10 = 6
So 111-12-6 is a valid CAS Registry Number.
InChI:InChI=1/C9H14O2/c1-3-4-5-6-7-8-9(10)11-2/h3-6H2,1-2H3
111-12-6Relevant articles and documents
Lead(IV) Acetate Oxidations of 3-Substituted and 3,4-Disubstituted 2-Pyrazoline-5-ones: A Facile Synthesis of 2-Alkynoic and 2,3-Alkadienoic (Allenic) Esters
Myrboh, B.,Ila, H.,Junjappa, H.
, p. 1100 - 1102 (1982)
-
Palladium-catalyzed carbonylation of terminal acetylenes: A new method for synthesis of acetylenecarboxylates
Li,Jiang,Chen
, p. 199 - 202 (2001)
Acetylenecarboxylates were easily prepared via palladium bromide-catalyzed carbonylation of terminal acetylenes in fair to good yields.
Synthesis of the ω6 (5z,8z)-tetradecadienoic and (7z,10z)-hexadecadienoic polyene fatty acids
Golovanov,Ganina,Groza,Eremin,Myagkova
, p. 26 - 30 (2015)
An approach using acetylenes was used and optimized to synthesize rare natural ω6 polyene fatty acids. The key synthetic step was cross-coupling of a propargyl derivative with a terminal acetylene in the presence of equimolar amounts of Cu(I).
Palladium-catalyzed oxidative carbonylation of 1-alkynes into 2-alkynoates with molecular oxygen as oxidant
Izawa, Yusuke,Shimizu, Isao,Yamamoto, Akio
, p. 2033 - 2045 (2007/10/03)
A new preparative method to produce alkyl 2-alkynoates from 1-alkynes in alcohol under atmospheric pressure of CO at room temperature was developed with palladium-phosphine catalysts, using molecular oxygen as an oxidant. On the basis of the behavior of model complexes such as methoxycarbonylpalladium and alkynylpalladium complexes, we propose a mechanism accounting for the catalytic carbonylation of alkynes through an intermediate having the both methoxycarbonyl and alkynyl ligands that liberates methyl 2-alkynoates and a Pd(0) species on reductive elimination. The oxidation of Pd(0) to Pd(II) species in the presence of a halide ion was confirmed to proceed cleanly with molecular oxygen as the oxidant. On the basis of the findings on homogeneous catalysts, a heterogeneous catalytic system using Pd/C has also been developed.