Vanillin, the major constituent of vanilla beans, is one of the most important aromatic flavor compounds used in foods, beverages, perfumes, and pharmaceuticals and is produced on a scale of more than 10 thousand tons per year by the industry through chemical synthesis.
Subscribe to a FREE Supplement Research Update newsletter. Once or twice a month we email a brief abstract of several studies on various supplements and natural medicine topics, including vanillin and spices, and their practical interpretation by Ray Sahelian, M.D.
Chemistry of Vanillin
Ferulic acid is an extremely abundant, preformed phenolic aromatic
chemical found widely in nature. Ferulic acid is viewed as a commodity
scale, renewable chemical feedstock for biocatalytic conversion to other
useful aromatic chemicals.
Vanillin (4-hydroxy-3-methoxybenzaldehyde), vanillic and protocatechuic acids are catabolic products
of ferulic acid degradation. Several substances can convert into vanillin.
Most attention is focused on bioconversions of ferulic acid to vanillin. Isoeugenol can also be converted into
ferulic acid and then on to vanillin.
Benefits of Vanillin
Like many
polyphenols found in plants, vanillin has
antioxidant and anti-tumor
activity.
Vanillin Research Update
Vanillin suppresses in vitro invasion and in vivo metastasis of
mouse breast cancer cells.
Eur J Pharm Sci. 2005 May;25(1):57-65.
Vanillin, a food flavoring agent, has been reported to show
anti-mutagenic activity and to inhibit chemical carcinogenesis. In this
study, we examined the effect of vanillin on the growth and metastasis of
4T1 mammary adenocarcinoma cells in BALB/c mice. Mice orally administered
with vanillin showed significantly reduced numbers of lung metastasized
colonies compared to controls. In vitro studies revealed that vanillin, at
concentrations that were not cytotoxic, inhibited invasion and migration
of cancer cells and inhibited enzymatic activity of MMP-9 secreted by the
cancer cells. Vanillin also showed growth inhibitory effect towards cancer
cells in vitro. However, vanillic acid, a major metabolic product of
vanillin in human and rat, was not active in these in vitro activity
assays. Our findings suggest that vanillin has anti-metastatic potential
by decreasing invasiveness of cancer cells. Since vanillin is generally
regarded as safe, it may be of value in the development of anti-metastatic
drugs for cancer treatment.
Inhibition of peroxynitrite-mediated
reactions by vanillin.
J Agric Food Chem. 2004 Jan 14;52(1):139-45.
Several neurodegenerative diseases such as Alzeimer's and Parkinson's
as well as septic shock and inflammation involve formation of reactive
oxygen and nitrogen species that include peroxynitrite (PON). PON can also
react with endogenous antioxidants. Therefore, dietary supplementation
with antioxidants may help in these diseases. An exogenous antioxidant,
vanillin (4-hydroxy-3-methoxybenzaldehyde), used widely as a food
flavoring agent, was evaluated for its ability to scavenge PON and inhibit
PON-mediated reactions. Nitration of tyrosine by PON was assessed by
high-performance liquid chromatography (HPLC). This reaction was inhibited
by vanillin. The oxidation of dihydrorhodamine 123 to fluorescent
rhodamine 123 was also inhibited by vanillin. The kinetics of reaction
between PON and vanillin was studied by stopped-flow technique. The
products of this reaction were analyzed by HPLC, and hydroxyvanillin was
identified as one of the five products with absorption at 350 nm. These
data demonstrate that vanillin effectively scavenges PON in cell-free
systems.
Vanillins -- a novel family of DNA-PK inhibitors.
Nucleic Acids Res. 2003 Oct 1;31(19):5501-12.
Non-homologous DNA end-joining (NHEJ) is a major pathway of double
strand break (DSB) repair in human cells. Here we show that vanillin
(3-methoxy-4-hydroxybenzaldehyde)--a naturally occurring food component
and an acknowledged antimutagen, anticlastogen and anticarcinogen--is an
inhibitor of NHEJ. Vanillin blocked DNA end-joining by human cell extracts
by directly inhibiting the activity of DNA-PK, a crucial NHEJ component.
Inhibition was selective and vanillin had no detectable effect on other
steps of the NHEJ process, on an unrelated protein kinase or on DNA
mismatch repair by cell extracts. Subtoxic concentrations of vanillin did
not affect the ATM/ATR-dependent phosphorylation of Chk2 or the S-phase
checkpoint response after ionising radiation. They significantly
potentiated the cytotoxicity of cisplatin, but did not affect sensitivity
to UVC. A limited screen of structurally related compounds identified two
substituted vanillin derivatives that were 100- and 50-fold more potent
than vanillin as DNA-PK inhibitors. These compounds also sensitised cells
to cisplatin. The inhibition of NHEJ is consistent with the antimutagenic
and other biological properties of vanillin, possibly altering the balance
between DSB repair by NHEJ and homologous recombination.
Vanillin supplier
December 2006 - Borregaard Ingredients announces an immediate 20% price increase
for its vanillin and ethyl vanillin product lines. The increase is the result of
significant higher costs (energy and raw materials) and imbalance between demand
and supply capacity. The shortage of vanillin is caused by a significant drop of
world capacity after shut down of two major Chinese producers along with a
globally increased demand. More than 2000 MT capacity has disappeared from the
market this autumn. The remaining Chinese producers increased the prices for
vanillin and ethyl vanillin approximately 20% in September. This has lead to a
tremendous increase in demand for vanillin and ethyl vanillin from other
sources. “We are sold out the next 3 months. For users of vanillin and ethyl
vanillin without contracts it will not be a question of what price they get, but
what volume they will be able to source from the market” says Thomas Grys,
Director of Borregaard’s vanillin business.
Vanillin emails
Q. My comment and question is this: I started drinking green tea as a
replacement for coffee. I still get some caffeine which has eliminated any
withdrawals. But green tea is terribly boring alone so I added an herbal
tea from Celestial Seasonings called Madsgascar Vanilla Red. It smells
wonderful and the taste is also pleasant. But after a few weeks I noticed
an increase in libido. Not a dramatic increase but yet still noticable.
Can green tea have this effect. Or is it the vanilla? Or is it a
combination of the two.
A. This is difficult to say, but many herbs have libido
enhancing properties, some are subtle and take weeks to work whereas
others can work in an hour or a day and are called aphrodisiacs. it could
be either the green tea, vanilla, or both.
Q. I came across your vanillin site while looking for additional information on vanillin. Were you aware that vanillin (synthetic vanilla) or 4-hydroxy-3-methoxybenzaldehyde is metabolized the phase II detoxification system in the liver, specifically glucuronidation? From Wikipedia, the free encyclopedia: Glucuronidation is a major inactivating pathway for a huge variety of exogenous and endogenous molecules, including drugs, pollutants, bilirubin, androgens, estrogens, mineralocorticoids, glucocorticoids, fatty acid derivatives, retinoids and bile acids. Those of us with Gilbert’s Syndrome experience severe reactions when ingesting vanillin. I personally experience profound debilitating fatigue with body temperature fluctuation as my temperature drops and I feel extremely cold. Although you may have listed some positive facts for vanillin on your website, I felt it was important to share what I have uncovered.
Q. Taking garlic can make one smell
really bad, but I've found taking vanilla makes me smell really good. When I put
a single drop of vanilla extract in my coffee just for flavor, I find that I
don't even need to wear deodorant. In fact, girls often comment on how good I
smell. Some say that I am "delicious." Wow! Is there a scientific basis to my
discovery? I mean, some of the stuff they put in deodorants can be downright
unhealthy. Wouldn't it be nice to be able to deodorize from the inside out?
A. Thanks for sharing this with us, it is a clever idea. Vanillin
may be the main chemical that smells nice.