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Vanillin

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Kathie Pham

on 29 April 2014

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Transcript of Vanillin

Vanillin
Synthetic Vanillin
industrial synthesis (up to the 1920s) began w/ eugenol which is found in cloves, nutmeg, etc.
today's vanillin is often made by reacting guaiacol with glyoxylic acid
biosynthesis: turn tyrosine into 4-coumaric acid, into ferulic acid, and then into vanillin
Questions
1. What are the three elements vanillin is composed of?

2. Where in the vanilla pod/bean is the vanillin released from?

3. Which synthesis method do we use today to produce synthetic vanillin?

4. What is the percentage of synthetic vanillin used in vanilla flavoring today?

5. What do people use to differentiate between synthetic vanillin and natural vanillin?
What is Vanillin?
organic compound found in vanilla
odorant molecule, meaning it is what gives vanilla its smell
important component of vanilla that makes up its taste also
biodegradable
"world’s most widely used flavor and frangrance ingredient" -Rhodia, Solvay
History
vanilla was discovered by Mayan and Aztec civilizations in Mexico and Central America
1858: Theodore Nicholas Gobley was the first to isolate vanillin by evaporating vanilla extract, then crystallize the remains
1874: Ferdinand Tieman and Wilhelm Haarmann studied its chemical structure, then opened a vanillin synthesizing industry
Molecular Properties
4-hydroxy-3-methoxybenzaldehyde

single molecule
colorless to slightly yellow solid
melting point of 81-83 degrees Celsius
boiling point of 285 degrees Celsius
Uses for Vanillin
For Flavor or Aroma
Naturally Made Vanillin
Kathie Pham
20 April 2014
Chemistry Per. 2

Answers
1. What are the three elements vanillin is composed of?
Cited Sources
Images
2.bp.blogspot.com/-jQFPUuEnXUM/UnCYFER0q-I/AAAAAAAAE-0/2_ax0LYf1jE/s1600/667px-Vanillin.svg.png
g.foolcdn.com/editorial/images/84612/artificial-vanillin-structure_large.png
i01.i.aliimg.com/img/pb/917/742/365/365742917_375.jpg
www.amadeusvanillabeans.com/pictures/images/vanilla-beans-vanillin-585.jpg
4.bp.blogspot.com/-6WFOfEYxc4U/UV3LkjEd_4I/AAAAAAAAAW0/kdskAeRbMCY/s1600/blog+aztec+mkt.jpg
upload.wikimedia.org/wikipedia/commons/6/6c/Theodore_Nicolas_Gobley_vers_1860_v2.JPG
upload.wikimedia.org/wikipedia/en/thumb/c/c7/Vanillin_crystals.jpg/450px-Vanillin_crystals.jpg
www.seriouseats.com/images/20100312-tjmacarons-vanilla.jpg
1.bp.blogspot.com/_40u3oW1Uq3A/S65a8ABU9GI/AAAAAAAACuo/bxVoiZei1MY/s1600/1953+vanilla2.jpg
upload.wikimedia.org/wikipedia/commons/thumb/b/b8/Vanillin.pdf/page1-220px-Vanillin.pdf.jpg
1.bp.blogspot.com/-izE4eUm3FCI/TfPk_Rx-MtI/AAAAAAAAGXk/S2qfdVuGLSk/s1600/vanilla.JPG
www.drugneed.com/images/product_images/info_images/IMG_6336.jpg
ecx.images-amazon.com/images/I/41DmMrnU85L._SX385_.jpg
www.foodsubs.com/Photos/imitationvanillaextract.jpg
plahutab.edublogs.org/files/2011/01/Vanillin-3d-2h1veqr-268x300.png
melodymeyerblog.files.wordpress.com/2013/11/real-vanilla.jpg
Fun Facts
found in a tropical orchid, known as
Vanilla Planifolia
, that grows on vines
vanilla pods are cured, turning into a deep brown, and resulting in a release of vanillin from the enzymes
makes up 2% of the mass of cured vanilla beans and 98% of the vanilla extract
In Medicine
75% of sweets, confections, and baked goods are made w/ vanilla
ingredient in coca-cola
cleaning materials (ex. soap)
often an ingredient in perfumes and fragrances
Madagascar and Indonesia currently have the largest vanilla crops
2010: annual demand was 12,000 tons but only 2,000 tons were naturally produced vanillin
Moctezuma, leader of the Aztecs, claimed Vanilla flavored drinks were good aphrosidiacs
Citations
"VANILLIN (4-HYDROXY-3-METHOXYBENZALDEHYDE)." <i>VANILLIN (4-HYDROXY-3-METHOXYBENZALDEHYDE)</i>. N.p., n.d. Web. 22 Apr. 2014. &lt;http://www.chemicalland21.com/lifescience/foco/VANILLIN.htm&gt;.

"Vanillin." - Reciprocal Net Common Molecule. N.p., n.d. Web. 22 Apr. 2014. <http://www.reciprocalnet.org/recipnet/showsamplebasic.jsp?sampleId=27344420>.

Colton, Simon. "Vanillin." <i>Vanillin</i>. N.p., n.d. Web. 24 Apr. 2014. &lt;http://www.rsc.org/chemistryworld/podcast/CIIEcompounds/transcripts/vanillin.asp&gt;.

Cotton, Simon . "VANILLIN." Vanillin. N.p., n.d. Web. 22 Apr. 2014. <http://www.chm.bris.ac.uk/motm/vanillin/vanillinc.htm>.

http://www.solvay.com/en/binaries/GPS_2011_12_v2_Vanillin_gb-139567.pdf
Carbon, Hydrogen, and Oxygen
2. Where in the vanilla pod/bean is the vanillin released from?
The enzymes
3. Which synthesis method do we use today to produce synthetic vanillin?
Biosynthesis Process of Producing Vanillin
Biosynthesis
4. What is the percentage of synthetic vanillin used in vanilla flavoring today?
95%
as flavoring
to produce L-dopa (chemical in human biology and is needed for chemical reactions)
to aid in treating Parkinson's disease by helping the body produce dopamine
is used in the heart drug papaverine
is used in antibacterial compound, trimethoprin
5. What do people use to differentiate between synthetic vanillin and natural vanillin?
chromatography
Continued.
molecular formula: C8H8O3
molecular weight: 152.15 g/mol
slightly soluble in water
sensitive to light
gradually oxidizes in contact with moist air
Natural & Synthetic
over 95% of vanilla flavoring today is made artificially
vanilla in most households are artificial
several methods to making vanillin synthetically
natural vanillin in vanilla can be sold at 200 times the cost of artificial vanillin
chromatography is used to identify synthethic vanillin from natural due to high radiocarbon levels in vanilla orchids
1. Guaiacol reacts w/ glyoxylic acid by electrophilic aromatic substitution (atom bonded to an aromatic hydrocarbon is replaced by an electrophile)
2. The product of that reaction is Vanillyl mandelic acid.
3. Using oxidative decarboxylation (reaction forming CO2), it's then converted to 4-Hydroxy-3-methoxyphenylglyoxylic acid
4. Converted to vanillin
Jeopardy Review
Easy 5 pts. Medium 10 pts. Hard 15pts.
What is the molecular formula for vanillin?
In what part of the vanilla plant is it found in?
____________ discovered vanillin in __________.
How does chromatography identify natural and synthetic vanillin?
How is vanillin used to aid in the treatment of Parkinson' disease?
In the biosynthesis process, guaiacol reacts with glyoxylic acid using what kind of chemical reaction? (Describe for an extra 5 points)
What is the percentage of artifical vanillin used in vanilla flavoring?
What are three uses for vanillin (other than in food)?
1.
2.
3.
What is vanillin's chemical name?
Full transcript