Synthesis of isotope-labelled methoxypyrazine compounds as internal standards and quantitative determination of aroma methoxypyrazines in water and wines by solid-phase extraction with isotope dilution-GC-MS /

An efficient way of synthesizing the deuterium labelled analogues of three methoxypyrazine compounds: 2-d3-methoxy-3-isopropylpyrazine, 2-d3-methoxy-3- isobutylpyrazine, and 2-d3-methoxy-3-secbutylpyrazine, has been developed. To confirm that the deuterium labels had been incorporated into the expected positions in the molecules synthesized, the relevant characterization by NMR, HRMS and GC/MS analysis was conducted. Another part of this work involved quantitative determination of methoxypyrazines in water and wines. Solid-phase extraction (SPE) proved to be a suitable means for the sample separation and concentration prior to GC/MS analysis.Such factors as the presence of ethanol, salt, and acid have been investigated which can influence the recovery by SPE for the pyrazines from the water matrix. Significantly, in this work comparatively simple fractional distillation was attempted to replace the conventional steam distillation for pre-concentrating a sample with a relatively large volume prior to SPE. Finally, a real wine sample spiked with the relevant isotope-labelled methoxypyrazines was quantitatively analyzed, revealing that the wine with 10 beetles per litre contained 138 ppt of 2-methoxy-3-isopropylpyrazine. Interestingly, we have also found that 2-methoxy-3-secbutylpyrazine exhibits an extremely low detection limit in GC/MS analysis compared with the detection limit of the other two methoxypyrazines: 2- methoxy-3-isopropylpyrazine and 2-methoxy-3-isobutylpyrazine.

Bright’s Wines Limited fonds, 1983-1989

One of the oldest wineries in Ontario, Bright’s Wines is now a part of Vincor International Inc. and still producing wines today. In the year 1874 Thomas G. Bright and Francis A. Shirriff came together in a partnership and formed a wine company in Toronto, Ontario. As the company began to prosper the gentlemen decided to move the location to Niagara, Ontario. Sixteen years later the Niagara Falls Wine Company opened on Dorchester Road. In 1911, Bright bought out all of Shirriff’s shares in the company and the name became the T. G. Bright and Co. Limited. A few years later in 1933 Harry C. Hatch bought the wine company from the Bright family and began changing how Bright’s operated through greater, more diverse wine production, as well as research and development. Bright’s leadership in wine research and development in Canada helped bring Canadian wines to their position of respect around the world. In 1934 Bright’s began a viticultural and vinicultural program, changing the way the Canadian wine industry worked. They put more money into research and development than any other winery in all of Canada. Soon, gold medals and “best of class” international designations were being awarded to Bright’s wines. As a result of their success, the founders soon discovered that they needed additional money to develop their business. So they borrowed money from a local bank and other lenders, or creditors, and used the funds to expand the business. Subsequent acquisition of other companies and consolidations in the wine industry led to the creation of Vincor International in 1993. Today, Vincor has established itself as a major participant in the North American super-premium wine market. By acquiring other companies, Vincor has fuelled growth in its sales from $114 million in 1995 to $654 million in 2005. The company’s success attracted the attention of its competitors. On September 27, 2005, Constellation Brands, Inc. announced its intention to buy Vincor and subsequently acquired the company in June 2006.

Barnes Wines: Canada’s Oldest Winery flyer. n.d.

In 1873 George Barnes, Andrew Skinner, James Skinner, John Young Reid, Charles Robert Murray, George Magan, Thomas Barnes and Robert Duncan applied for, and received a charter for a commercial winery which would be called The Ontario Grape Growing and Wine Manufacturing Company Limited. It opened in 1894 and became known as Barnes Wines Limited. In 1973 the company completed a merger with Reckitt and Coleman (Canada) Limited. The winery operated until 1988 and was located on the banks of the old Welland Canal in St. Catharines, Ontario. The company produced a complete line of table wines, dessert wines, sherries, ports, and both crackling and sparkling wines. Barnes Wines called itself “Canada’s oldest winery” at the time of the printing of this flyer.

Barnes Wines Fonds

4 Minute Books dated: 1880, 1892, 1901, 1934, 1948-1950, 1952-1953, 1955, 1958, 1962 – 1975, 1981, 1984, 1986; 3 Common stock books dated: 1934-1935, 1937-1941, 1946, 1948-1950, 1955-1956, 1958, 1961-1974, 1981 and 2 Class A stock books dated:1948 - 1951

METHOXYPYRAZINES AND LADYBUG TAINT IN WINES

Methoxypyrazines are aroma active compounds found in many wine varietals. These compounds can be of either grape-derived nature or can be introduced into wines via Coccinellidae beetles. Regardless of their origin, methoxypyrazines can have either a beneficial role for wine quality, contributing to the specificity of certain wine varietals (Cabernet sauvignon, Cabernet franc, Sauvignon blanc) or a detrimental role, particularly at higher concentrations, resulting in overpowering green, unripe and herbaceous notes. When methoxypyrazines of exogenous nature are responsible for these unpleasant characteristics, wines are considered to be affected by what is generally known as Ladybug taint (LBT). This is work is a collection of studies seeking to create a sensitive analytical method for the detection and quantification of methoxypyrazines in wines; to investigate the role of different Coccinellidae species in the tainting of wines with LBT and identify the main compounds in ladybug tainted wines responsible for the typical green herbaceous characteristics; to determine the human detection threshold of 2,5-dimethyl-3-methoxypyrazine in wines as well as investigate its contribution to the aroma of wines; and finally to survey methoxypyrazine concentrations in a large set of wines from around the world. In the first study, an analytical method for the detection and quantitation of methoxypyrazines in wines was created and validated. The method employs multidimensional Gas Chromatography coupled with Mass Spectrometry to detect four different methoxypyrazines (2,5-dimethyl-3-methoxypyrazine, isobutyl methoxypyrazine, secbutyl methoxypyrazine and isopropyl methoxypyrazines) in wine. The low limits of detection for the compounds of interest, improved separation and isolation capabilities, good validation data, as well as the ease of use recommend this method as a good alternative to the existing analytical methods for methoxypyrazine detection in wine. In the second study the capacity of two Coccinellidae species, found in many wine regions – Harmonia axyridis and Coccinella septempunctata - to taint wines is evaluated. Coccinella septempunctata is shown to be as capable as causing LBT in wines as Harmonia axyridis. Dimethyl methoxypyrazine, previously thought to be of exogenous nature only (from Coccinellidae haemolymph), is also detected in control (untainted) wines. The main odor active compounds in LBT wines are investigated through Aroma Extract Dilution Assay. These compounds are identified as isopropyl methoxypyrazine, sec- and iso- butyl methoxypyrazine. In the third study, the human detection threshold for dimethyl methoxypyrazine in wine is established to be 31 ng/L in the orthonasal modality and 70 ng/L retronasally. After wines spiked with various amounts of dimethyl methoxypyrazine are evaluated sensorally, dimethyl methoxypyrazine causes significant detrimental effects to wine aroma at a concentration of 120 ng/L. The final study examines methoxypyrazine (dimethyl methoxypyrazine, isopropyl methoxypyrazine, secbutyl methoxypyrazine and isobutyl methoxypyrazine) concentrations in 187 wines from around the world. Dimethyl methoxypyrazine is detected in the majority of the red wines tested. Data are interpreted through statistical analyses. A new measure for predicting greenness/herbaceousness in wines - methoxypyrazine “total impact factor” is proposed.

The Vintners Quality Alliance - VQA Officially Launches its "Appellation of Origin" System for Ontario Wines, June 27 1989

An official launch for the '"Appellation of Origin" System for Ontario Wines'. The VQA announces the labeling system which will identify "Ontario wines based on the origin of the grapes from which they are produced". The system relies on Provincial and Geographic Designations which are outlined in the announcement.

Inniskillin Award Winning Wines - '98-'02

A list of awards for Inniskillin wines for the years 1998-2002.

Inniskillin Wines at Macy's New York for Ontario Fine Foods Promotion

A letter from Export Development Officer, Kenneth M. Mueller which is part of a large photo album, dated May 9, 1986. The letter indicates that Mueller put together the album showing the reception at the Trillium Room and the Macy's Marketplace presentations. The promotion was for Ontario fine products and included Inniskillin. The photograph featured from the album shows Donald Ziraldo at his Inniskillin table in the Trillium room talking to patrons of the event.

Barnes Wines, Limited, Shares Certificate, 1957

Share certificate No. BP001, registered to Mrs. Bessie A. Barnes Barkley. The certificate has several shares transactions listed. The final number of shares redeemed on April 11th, 1957 is 316.

Barnes Wines, Limited, Shares Certificate, 1934

A shares certificate issued to The National Trust Company for two hundred shares.

Barnes Wines, Limited By-Law no. 82

A by-law "to fix the remuneration and expense allowances of directors". It reads "Be it enacted as a By-law of Barnes Wines Limited: 1. That each Director of the Company be paid the sum of Seventy-five ($75,00) Dollars annually in respect of general services rendered by the Director in his capacity as Director, such remuneration to accrue from the date of his election or appointment as a Director. 2. That each Director shall be paid and allowed travelling and other expenses properly incurred in connection with the affairs of the Company. 3. That this provision shall be and remain in force and effect in the fiscal years of the Company, 1971 to 1973 both inclusive. Enacted this 8th day of February, 1971."

Barnes Wines, Limited, Special Resolution No.1

The note at the start of the resolution reads: "A special resolution to authorize an application for supplementary letters patent varying the authorized capital of the company by re-classifying and changing certain shares and increasing the capital of the company by the creation of additional preference shares".

Barnes Wines, Limited By-Law Index

A list of company by-laws starting July 1873 through April 1973.

Barnes Wines, Limited By-Law no. 75

By-Law no. 75 begins "A by-law to govern the affairs of the company and repealing the by-laws of the company passed heretofore relating to the administration of the affairs of the company".