Vanillyl alcohol

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Structural formula
Structure of vanillyl alcohol
General
Surname Vanillyl alcohol
other names

4-hydroxy-3-methoxybenzyl alcohol

Molecular formula C 8 H 10 O 3
Brief description

white or colorless crystals with a mild, sweet, vanilla-like odor

External identifiers / databases
CAS number 498-00-0
EC number 207-852-4
ECHA InfoCard 100.007.140
PubChem 62348
ChemSpider 56139
DrugBank DB12087
Wikidata Q2510417
properties
Molar mass 154.17 g mol −1
Physical state

firmly

Melting point

114-115 ° C

solubility
  • little in water (2 g l −1 at 20 ° C)
  • good in oils
safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Vanillyl alcohol ( 4-hydroxy-3-methoxybenzyl alcohol ) is an organic chemical compound naturally found in Sitka spruce ( Picea sitchensis ). The substance is structurally derived from both benzyl alcohol and guaiacol ( o -methoxyphenol). The white or colorless crystals with a mild, sweet, vanilla-like odor dissolve only slightly in water, but dissolve well in oils.

A catalytic hydrogenation of vanillin leads to vanillyl alcohol or 2-methoxy-4-methylphenol .

The vanillyl-alcohol oxidase catalyzes the oxidation of various phenolic compounds, especially many 4-alkylphenols. The oxidation of vanillyl alcohol to vanillin was originally demonstrated in vitro :

Vanillyl alcohol+ O 2Vanillin+ H 2 O 2

Vanillyl alcohol is classified as FEMA GRAS ( G enerally R ecognized A s S afe , FEMA GRAS # 3737) in the United States and can therefore be used there as a food additive .

See also

Individual evidence

  1. a b c Shmuel Yannai: Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. CRC Press , 2003, ISBN 978-1-58488-416-3 , p. 307.
  2. a b D. C. Ayres (Ed.): Dictionary of Natural Products, Volume 6. CRC Press , 1994, ISBN 978-0-412-46620-5 , p. 1562.
  3. Entry on vanillyl alcohol in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  4. a b Data sheet Vanillyl alcohol from Sigma-Aldrich , accessed on April 25, 2011 ( PDF ).
  5. Fragrance Lexicon: Vanillin .
  6. A. Mattevi, MW Fraaije, A. Mozzarelli, L. Olivi, A. Coda, WJ van Berkel: Crystal structures and inhibitor binding in the octameric flavoenzymes vanillyl-alcohol oxidase: the shape of the active-site cavity controls substrates specificity , in: Structure , 1997 , 5  (7), pp. 907-920 ( PMID 9261083 ; full text ).
  7. George A. Burdock: Encyclopedia of food and color additives, Volume 3. CRC Press , 1997, ISBN 978-0-8493-9414-0 , p. 2903.

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