102

SYNTHETIC MEAT FLAVORS*

IRA KAT2 Internat ional Flavors & F'ragrances, Inc.

There i s l i t t l e doubt that from a technical standpoint the flavor industry has advanced more i n the past two decades than i n a l l previous h is tory . Today, completely synthetic fruit flavors car, = - -rested t h a t possess the odor and f lavor of e i the r f resh o r cooked f r u i t . f lavor chemists have the capabi l i ty and "tools" t o duplicate the metall ic canned character that i s c b r a c t e r + . s t i c of many of our canned f r u i t s . Thus, not only has t he f lavor chemist duplicated nature but he is a l so concerned with duplicating f lavors t h a t a r e a r e s u l t of modern food technology. food technologists is resulting i n the duplication of many whole foods, especial ly those being used as r a w materials by the food industry. Synthetic dry and w e t cheeses, synthetic t o m t o powder a re r e a l i t i e s today. be added t o the l i s t according t o the d i c t a t e s of world economic conditions.

Creative

Combining the t a l e n t s of the flavor chemist with modern

These t o t a l synthetics w i l l improve i n qual i ty and others w i l l

Unfortunately, synthetic meat f lavors have not yet a t ta ined the s t a t e of the a r t t h a t ex i s t s fo r c i t r u s and f r u i t f lavors . This is not because th i s important area of research has been neglected but, ra ther because reaching a complete understanding of the colnplexity of the chemistry of the var ie ty of types of meat and poultry f lavors i s one of the most d i f f i c u l t and challenging problems of modern flavor chemistry. The complete understanding of meat chemistry requires the combined e f fo r t s and t a l e n t s of ana ly t ica l chemists, organic synthetic chemists, creative f lavor chemists and food technologists. doubt that t h i s area of research is now being emphasized by every progressive f lavor cmpany. be successfully applied t o meat analogs a r e providing the impetus and ju s t i f i ca t ion f o r t h i s research.

I believe t h a t there i s l i t t l e

The huge poten t ia l markets t h a t await f lavors t h a t can

Table 1 shows U.S.D.A. 190 market penetration projections f o r soy protein products i n the meat area (1). proJections that the immediate market fo r t he next 10 years is ground beef products. 3 b i l l i o n pounds which t r a n s l a t e s t o 2 million head of c a t t l e and calves and 4 million head of hogs or, 44 of the estimated 1980 production. The major impetus f o r p a r t i a l meat replacements a re lower r e t a i l pr ices and a t l ea s t i n the U.S., d i e t s containing lower cholesterol and saturated fa ts . Table 2 i l l u s t r a t e s the cost savings that can be real ized when 20 and 4 6 of the meat I n hamburgers is replaced w i t h extruded soy protein. The calculations assume 1.00 do l l a r per pound f o r boneless chuck and 25

It i s apparent from these

Notice t h a t t h e t o t a l meat replaced is approximately

* Presented a t the 26th Annual Reciprocal Meat Conference of the American Meat Science Association, 1973.

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cents per pound f o r dry extruded soy. It is our opinion that the long term success and consumer acceptabi l i ty of these products, especial ly a t the 40 and 5c$ replacement levels , where extremely a t t r a c t i v e r e t a i l pr ices a re realized, is dependent upon t h e production of texturized protein t h a t is bland i n f lavor, and the ava i l ab i l i t y of synthetic meat f lavors t h a t function in these systems and impart a high quality, t r u e meat f lavor t o the product.

The poten t ia l use of meat analogs is obviously not limited t o the U.S. Over the Next 20 Years'' ( 2 ) i l l u s t r a t e s the estimated production of major protein sources i n the United Kingdom. Notice t h a t by 1983 f resh meat production is projected t o be l eve l while vegetable protein production continues t o increase rapidly.

As a n example, f igure 1 taken from "Trends i n the Food Industry

The first synthetic meat flavors sold by the f lavor industry were undoubtedly s k i l l f u l spice blends that were and s t i l l a re used i n processed meats. 5' nucleotides became recognized and available, they were combined w i t h spices t o supply a portion of the brothiness of meat and t o enhance the f lavor of the na tura l meat. The introduction of high qual i ty hydrolyzed vegetable proteins, which were then canbined w i t h the nucleotides and spice blends, resul ted i n t he f i rs t meat f lavors i n cer ta in areas of the food industry. For example, i n the U.S., hydrolyzed vegetable protein products have almost completely eliminated the use of beef extract i n dry soup, boullions, canned soups, and gravies. This replacement was brought about by economic conditions which resulted i n increased costs of beef ex t rac t along w i t h a consistent lowering in qual i ty . There i s no doubt that hydrolyzed vegetable protein based flavors a r e Ea7 f r o m duplications of beef extract , but t h e i r gradual introauctron and consumer acceptabi l i ty have resul ted i n a change i n t he f lavor standards of the American consumer t o an extent that many people doubt t h a t beef ex t rac t could be re-introduced i n the products where it has been replaced by hydrolyzed vegetable protein.

Once the importance of monosodium glutamate and the

As good as these f lavors ase, they a re a long way f romthe type and qua l i ty f lavor needed by the Food Industry f o r today's expanding meat replacement market. projected a need f o r t r u e synthetic meat f lavors , industry research i n th i s area began a t t h i s time. I n 1960 the pioneering work 3' 2atzer et &. (3) resul ted i n the i s o h t i o n of a glycoprotein frm the aqueous ex t rac t of r a w beef which, upon heating i n the presence of a nucleotide developed a meaty aroma. Thus, t he important concept wa8 brought forth t h a t the basic meat aroma w a s due t o the chemical interact ion of water soluble precursors. Other investigations by numerous groups led t o the conclusion that the development of meat flavor and aroma is , a t l e a s t i n part, due t o a Maillard type reaction. As a r e su l t , raw beef has been thoroughly analyzed f o r i t s amino acid and reducing sugar content and many combinations have been formulated and subjected t o various cooking conditions i n an attempt t o duplicate the cooked beef aroma and f lavor . I n an attempt t o capi ta l ize upon t h i s basic information, a large number

Since marketing predictions during the 1950's

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of patents have been g r a d e d that a r e essent ia l ly products by pmcess . Table 3 summizes some of the numerous patents t h a t have been granted in this area .

These patents are only a small percentage of the exis t ing patents t h a t teach the production of meat f lavors by reacting water soluble ingredients. great dea l of commercial success i n cer ta in areas, they are not the f i n a l answer i n meat f lavors . commercially viable f o r many years, they are essent ia l ly "stop-gap'' measures u n t i l the next generation of meat f h v o r s becomes avai lable . I n order t o place synthetic meat flavors on the same l eve l as f r u i t f lavors , the creat ive f l avor i s t must have available t o him, the individual chemicals responsible f o r the arcam and t a s t e of cooked beef. Only then can h i s creat ive t a l e n t s be f u l l y u t i l i z e d . Thus, we f ind today i n both the technical and patent l i t e r a t u r e a rapid movement toward the ident i f ica t ion and u t i l i z a t i o n of individual chemicals with meat - l ike f lavors . These are s t ruc tu ra l ly d i f f e ren t than most of the chemicals used by the f lavor chemist today and en t i r e ly new synthetic and creative learning processes must evolve i n order t o apply and commercialize t h i s new generation of meat f lavors .

Although many of these flavors have undoubtedly enjoyed a

A l t h o u g h f lavors of t h i s type w i U remain

The f i rs t report of unique aromatic chemicals i n boiled beef w a s i n 1968 when Chang and co-workers (4) reported the ident i f ica t ion of two heterocyclic compounds. These chemicals, which a re shown i n f igure 2, a r e 2,5-trimethyl-delta-3-oxazoline and 2,4,5-dimethyl-1,2,4-trithiolane. Although the or igin of these compounds is unknown, t he oxazoline could form from the reaction of acetoin, acetaldehyde and annnonia, a l l of which a r e present during the cooking of beef. Indeed, it i s synthesiTded i n the laboratory with r e l a t ive ease i n t h i s manner. The t r i t h io l ane could come from the reaction of acetaldehyde and hydrogen sulf ide; however, the recent report of another new aromatic chemical i n boiled beef provides a more a t t r a c t i v e pathway. and Wilson and co-workers (6) a t IFF' reported the i so la t ion of thialdine in boiled beef ( f igure 3 ) . t he t r i t h io l ane during i so la t ion and more l i k e l y during the cooking process. ammonia and hydrogen su l f ide .

In 1972 Brinkman and co-workers ( 5 ) at Unilever,

This unstable chemical w i l l decompose t o form

Thialdine could arise f r o m the reaction of acetaldehyde,

I n addition t o these cycl ic sulf'ur cmpounds, Wilson c ; -1. (6) reported the ident i f ica t ion of two other new polycyclic sulfur chemicals, namely t r i thioacetone and tri thioacetaldehyde (figure 4 ) . chemicals were ident i f ied i n cooked beef.

Both of these

Other new al i$at ic su l fur chemicals t ha t have been isolated from boiled beef a re 1-methylthio-ethanethiol ( 5 ) , 3-methyl-2-butanethiol (6), and 2-methyl-1-butanethiol (6) . report of 2-acetyl thiazol ine i n beef by Unilever workers in 1971 (7) .

Another chemical of i n t e re s t is the

108

TABLE 3. PROCESSED MFAT FLAVOR PATENTS

Morton, U.S. 2,934, AToyd, 37 (Lever); May 2,934,436

Giacino (IFF) U.S. 3,394,015; 3,394,016

Giacino (IFF) U.S. 3,519,437

Perret, Perret and McMahon (Pf i ze r ) U .S . 3,365,306; 3,271,167

Hack and Konigsdorf (CPC) U S . 3,480,447

O ' H a r a , Ota, Enej, Eguchi, Okumura (Ajinomoto) U . S . 3 9 524,747

Broderick and Marcus (11. Kohns tm) U.S. 3,532,525

~ a y , Soeters (Lever) U.S. 3,532,514; 3,493,395

Tonsbeek (Unilever ) Canadian 862,685

Reducing Sugar or Glyceraldehyde 1960 + Cysteine + H20 120° f o r two hours

HVP + cysteine + thiamirs ' 1968 H20 + heat at llO-l5@

T a x i n e + thiamine + HVP + 1970 H 2 0 or fa t + heat + flash heating

Reducing sugars or alpha- 1968 ketobutyric acid, cysteine o r methional + H 0 + heat; then add HVP and & and heat again f o r two hours

Amino acids (no cysteine) HW + reducing sugar + taur ine + heat 1100 for 15-20 hours

Amino acid (not cysteine) + l ac t ic acid + phosphate + nucleotide-5 -phosphate

Cysteine + 5'=nucleotide + H 2 0 + heat

Reducing sugar + cysteine + 1970 fa t + TO0 f o r 24 hours or 140° u n t i l water-free

Amino acids + lact ic acid + 1971 5 -nucleotide + heat llO-l5OO

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All of the chemicals that I have discussed were found f o r the first time i n nature through the investigation of cooked meat f lavor . hundreds of other chemicals t h a t have been found i n other heated foods such as coffee, nuts and chocolate have a l so been reported i n beef. include a l ipha t ic sulf ides , f b r m s , thiophenes, thiazoles , pyrazines, aldehydes, ketones, enals and dienals .

L i te ra l ly ,

These

Time does not permit me t o discuss these, but cer ta inly they a re important t o the creation of synthetic meat f lavors .

Another group of chemicals that are important f o r meat flavors are chemicals t h a t a r e meat-like i n fl ivor but do not necessarily occur i n beef. careful reading of the patent l i t e r a t u r e . few of the more in te res t ing patents and applications.

An awareness of these m a t e r i R l s can only be obtained through I would l i ke t o mention a

In 1968, Tonsbeek e t -- a l . (8) reported the ident i f ica t ion of t w o furanones f o r the f i rs t time in beef. These chemicals a re shown i n figure 5 . t he dimethyl compound w a s previously reparted t o OCCUT i n pineapple.

Both of these chemicals a r e in te res t ing f lavor chemicals and

In 1969, IFF f i l e d f o r patents on a group of f'urans that possess a meat-like f lavor . a r e sham i n figure 6 .

A number of chemicals t h a t a r e typ ica l of t h i s patent

Shortly thereaf te r , both Unilever and IF'F applied f o r patents that teach the reactions of t he dimethyl furnanone, previously reported t o occur i n beef, w i t h hydrogen su l f ide t o form meat f lavors .

Unilever has reported ( 9 ) that t h e m a n s and thiomenes shown i n f igure 6 a re formed as a result of t he reaction. Although these chemicals and the furanthiols i n the IFF patents have not been ident i f ied in meat or other heated foods, everything points t o the f a c t that they are present and t h e i r discovery in a na tura l system i s a challenge t o the modern ana ly t ica l f lavor chemist.

Another in te res t ing chemical that is the subject of an IF'F patent application is the discovery that dimethyl dihydroxy dithiane has a roast chicken f lavor . This chemical i s in te res t ing in that it forms from mercapto acetone a t ambient temperature ( f igure 7). revers ible upon heating and mercapto acetone is formed. The mercapto acetone and other alpha keto mercaptans have intense meat-like aromas and a re the subject of other IFF patents.

The reaction is

In conclusion, the intense investigatlan of meat flavors has led t o the discovery of a grea t number of individual chemicals that when used alone or, in combination w i t h t he previous synthetic meat f lavors , w i l l r e s u l t i n the creation of synthetic meat flavors t h a t will surpass the meat flavors found on today's market.

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REFERENCES

1. Marketing Research Report No. 974 U . S . Department of Agriculture Economic Research Service (19721.

2 . Trends in the Food Industry Over the Next Twenty Yews, A Delphi Banfield, F. H . e t -- al. Exercise in Technological Forecasting.

(Bri t ish Food Manuf . Ind . Res. Assn ., Leatherhead , 2 , ~ . ) 1971-1972.

3 . Batzer, 0. F., A . T. Santoro, M. C . Tan, W. A . Landman and E. S. Schweigert . J. Agr . Food Chcm. 8 :498 1960.

4. Chang, S. S., C . Harai, B. R. Reddy, K. 0 . Herz and A . Kato. 1968. Chem. and Ind. p. 1639.

5 . BrinlaPan, H.I.U., H . Copier, J.J.M. dekuco and S. B. Tjan. 1972. J. Agr. Food Chm. 20:177.

6 . Wilson, R. A . , C . J. Mussinan, I. Katz and A. Sanderson. 1973. J. Agr. Food Chem. 21.

7. Tonsbeek, C.H.T., H. Copier and A . J. Plancken. 1971. J. Agr. Food Chem . 19 : 1014.

8 . Tonsbeek, C.H.T., A . J. PLascken and T. van der Weerdhof.

van der W e l a n d and Peer (Unilever) West Germany 1,932,800.

1968. J. Agr. Food Chem. 16:1916.

9 .

BILL SULZBACHER: I a m a l i t t l e b i t disturbed that t h e cured meat f lavor i s due only t o the antioxidant a c t i v i t y of the n i t r i t e s . I r e c a l l t h a t a number of years ago when we were working on cured meats w e cured some pork, lanib, rabbit and beef and gave them t o our t a s t e panel without ident i f ica t ion and t h e t a s t e panel was unable t o dis t inguish between these meats o r the species. spec i f ic t o meat flavor; it wasn't just a matter of antioxidant ac t iv i ty . There was a n ac tua l contribution of n i t r i t e t o the f i n a l f lavor .

It always seemed t o me that n i t r i t e did something

Another t h h g occurs t o me as a problem.

You s t i U . get t h i s very charac te r i s t ic You can' t say that it tastes anything l i k e f resh beef .

what about corned beef, where you cure it i n an e s sen t i a l ly anaerobic manner and it i s n ' t cured very long and you don't smoke it. change i n f lavor . I ' d l i k e t o hear t h i s ta=d around a l i t t l e b i t and h e w what other people think.

DUANE WESTERBEFG: I can make just one comment along *hat l i n e . There i s another great f ac to r that you put in to corn beef paper published along these l i nes . But w h a t e f fec t , actual ly , does seasoning have on the taste of the product7 compounds such as n i t r i t e , w h a t does seasoning contribute t o t h e final t a s t e of t he product7

I know of no

Again, eliminating some

AARON WASSEEMAN: What about the e f fec t of smoking? I think we have seen that n i t r i t e seems t o enhance smoke flavor. Have you any coments?

DUANE WESTERBEFG: The only comment I have i s that i n same of our work when we studied antioxidants we did smoke sane products w i t h arid without n i t r i t e , at l e a s t with zero and maximWm cure. We used .i 5 minute smoking cycle, measured by density with GE equipment, it would be about 8oqd. didn ' t see any difference w i t h and without the smoke.

We could ac tua l ly get the f lavor notes and aroma of smke and we

JAY FOX, USDA: The presence of oxides of nitrogen i n the air has long been known. We have been doing some color work and without using any smoke you can get a nice beautiful pink n i t r i c oxide color. l i k e t o suggest t h a t perhaps at the low levels used t o detect f lavor, the presence of any type of oxides of nitrogen with the subsequent poss ib i l i t y of n i t r i t e , almost any oxides you want t o name, could produce enough f lavor s o that you wouldn't have t o smoke it, n i t r i t e it, or anybhhg e l s e it. Now I wonder whether t h i s wouldn't have something t o do w i t h t a s t e panels sometimes having a l i t t l e d i f f i c u l t y t e l l i n g whether there is an ac tua l cured meat flavor; especial ly with scmething that has been put in to a smoke house.

I would

TOM BIUMER, NORTH CAROLINA STATE: There are several people here, I know, from Natick and they may not be at l i b e r t y t o comment, but D r . Gene Wierbicki was a t our place the other day and he had something on th i s n i t r i t e - n i t r a t e f lavor and I am not going t o comment on it but I know about it because I tas ted sane of the product. Natick group would be a t l i b e r t y t o speak on this or not.

I don't know whether the

AARON WASSEIiMAN: answer t o this7 Max7

Is there anyone here

MAX BROCKMA”, NATICX: I r e a l l y don’t but it is my understanding that Wierbicki’s

from Natick that wants t o

know very much about this, group has observed t h a t

i r rad ia ted meat has received a l l the benef i t s of- i r radiat ion w i t h subs tan t ia l ly l e s s n i t r i t e than is normally used. 1 imgine that i r r ad ia t ion seems t o compensate f o r a ce r t a in amount of the absence of n i t r i t e .

AARON WASSERMAN: Well, t h i s spew contrary-you should be get t ing more warmed-over f lavor w i t h al.’ %Lis i o n i z b g radiat ion and free-radical formation. Any comments on that, Harold?

TOM BWMER: I have one other question. How many methods would you indicate were su i tab le f o r running n i t r a t e and n i t r i t e . is a dynamic system and depends on w h a t kind of product you are conducting your analysis on as t o w h a t kind of recovery you ge t . number of methods I know that are being used and I’d like t o know which ones you think do the bes t job on quant i ta t ive re turns .

I how tha t th is

But there are a

AARON WASSEIIMAN: Do any of t h e panel have any coment on this7 This i s a l i t t l e off the subject we are talking about. Jay, would you l i k e t o c m n t 7

JAY FOX: We are trying t o f ind out where n i t r i t e s go and as part of our study we ran six di f fe ren t methods, which come h-ly recommended or are i n ac tua l use, and ccxnpared them w i t h the AOAC. W e used the one which EEC! (European Economic Comunity) is recommending o r using and a few others but the best r e su l t s we got were with the AOAC method. The standard deviations were e s sen t i a l ly the same, but the highest y ie ld was w i t h t he AOAC, and it was ha l f again to double what t h e other methods gave. method, too. We have a paper caning out i n the Ju ly issue of the JAOAC.

We also found there were some wierd discrepancies i n the AOAC

UNIDENTIFIED: W o u l d you care t o coment on the paucity of e f f o r t s on the oxidative changes i n phospholipids i n contrast w i t h the enormous m u n t of work t h a t has been done on the oxidation of neut ra l l ipids?

HAROLD HERRING: Most of the work on meat off-flavor development has been on the oxidation of the phospholipid f r ac t ion . occurs i s believed t o be due t o the phospholipid f rac t ion . ex t rac ts , fo r example, meat w i t h d ie thyl e ther , you s t i l l ge t very rapid oxidation of the meat residue; if you ext rac t with chloroform methanol the extraction removes any oxidisable l ipid. work does indicate the phosmolipid f rac t ion in the t i s sue is the cu lp r i t that has been disrupted, cooked o r ground.

The r ap id i ty which If one

I would think most of the

UNIDENTIFIED: D r . Katz showed us sane data on the amount of soy protein products t h a t a r e going t o replace meat products and D r . Herring had discussed ranc id i ty development. I have a question that i s going t o

cut across both of these areas i n the future . greater substi tution of meat w i t h soy proteins it seems that the subst i tute i s going t o have t o be supplemented with i ron . question-do we know how we are going t o supplement t h i s i n t e r n of chemical reactions and nut r i t ive value of the product that is produced?

When we go t o greater and

I would like t o r a i se the

IRA KATZ: be t o coat the iron t o protect from i t s action on t h e food.

I don't know; I am speculating, but one possibi l i ty may

KEN BEERY: For D r . Herring. On t he developnent of the warmed flavor-- apparently you have t o heat it just so much t o get developuent and i f you overheat it there w i l l be no d e v e l o w n t . temperatures below which you w i l l preclude developnent and above which w i l l preclude development.

What is the c r i t i c a l range of

HAROLD HERRING: In our experience there is no heat below which you w i l l have developent of warmed over f lavor . You have t o go t o s t e r i l i z i n g conditions t o get formation o f t h e canpounds in a canning system. Browning reaction, products will be formed a t 100°C or higher, preferably a t U O O .

I n a

I believe 1 understood ;you t o say e a r l i e r t h a t you had found i n deep fa t fried poultry no warmed over flavor and with subsequent micrarave cooking, warmed over f lavor . Is this correct?

KEN BEERY: The way it was reported was that with deep fat frying then finishing off with micrmave caused more developnent of warmed over f lavor than micrarave cooking up t o the same temperature then f inishing off w i t h deep fa t f'qdng. cooking methods that could help preclude this developmen%?

The intent of the question is--are there

HAROLD HERRING: It may have been the deep fat frying or the time i n which it was done tha t determined whether the i n i t i a t i o n of the reaction occurred. which were present i n i t i a l l y but which later may have volat i l ized. one m u s t be careful there .

And there may have been antioxidants i n the deep f a t frying o i l So

KEN BFERY: Microwave cooking the en t i re way caused l e s s warmed over f lavor than with combinations.

HAR3LD HERRING: With storage f o r how long?

KEN BEERY: This was a week's storage, I believe.

UNIDENTIFIED: I ' d like t o ask whether warmed over flavor has been confined t o ground beef and i f not how factors such as the s ize of the piece of meat, the storage i n frozen condition, whether the frozen meat i s wrapped in an oxygen permeable f i l m w o u l d af fec t the developent of t h i s warmed over flavor? Another question, how does pork compare w i t h beef i n the development of the flavor?

I20

HAROLD KERRING: Which pork? Fresh pork? It has been observed i n our laboratory i n beef, pork and poultry--turkey and chicken. action, disruption of t he c e l l , would expose phospholipids t o the act ion of oxygen and ca ta lys t s . Any anaerobic packeging say, f o r example, with chopped beef, pre-ground beef chopped beef, does inh ib i t t he reaction as long as it is kept anaerobic because the meat systems reduce any oxygen.

Any grinding

AARON WASSEIPIAN: We'll have time f o r one more question.

BOB KAUKWAN, WISCONSIN: This is dlrected t o D r . Katz. I ' d l i k e t o have ;yau review fo r me again your projection fo r u t i l i z a t i o n of vegetable protein versus animal protein i n the f'uture and I do have a question t o ask: H a s p r ice been considered i n t h i s prediction?

IRA KATZ: Pr ice has been considered. Here is the projection taken from the da ta projected b Marketing Service Report $94 7, Economic Research Service, USDA, 1972. The projections were one b i l l i o n pounds. a r e interested i n .

the U.S. Department of Agriculture--Agricultural

I don't know w h a t aspects you

BOB KlwFEMAN : Y o u showed me a figure, not a t ab le but a f igure.

IRA W Z : That was f o r the United Kingdm, nat the United S ta t e s .

BOB KAUFEMAN: Thank pu, I did not understand t h a t . What w a s the source of t h i s information?

I R A KATZ: This w a s essent ia l ly a published survey called, "Trends in the Food Industry." w a s arr ived a t was a survey of 50 people i n the food industry on w h a t they th ink w i l l happen 20 years from now or 10 years from now.

I can send you the reference. Really how t h i s