Perillaaldehyde

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Structural formula
Structural formula of (S) - (-) - perillaldehyde
Structural formulas of the ( R ) -form (left) and the ( S ) -form (right)
General
Surname Perillaaldehyde
other names
  • Perillaldehyde
  • ( RS ) - p -Mentha-1,8-diene-7-al
  • ( RS ) -4-isopropenyl-cyclohexene-1-carboxaldehyde
Molecular formula C 10 H 14 O
Brief description

yellow liquid

External identifiers / databases
CAS number
  • 5503-12-8 (+)
  • 6611-91-2 (±)
  • 18031-40-8 (-)
  • 2111-75-3 (-)
PubChem 16441
Wikidata Q3117895
properties
Molar mass 150.22 g mol −1
Physical state

liquid

density
  • 0.965 g cm −3 (S)
  • 0.953 g cm −3 (R)
boiling point
  • 104–105 ° C (13 hPa) (S)
  • 273 ° C (R)
Refractive index
  • 1.5069 (S)
  • 1.5058 (R)
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 . Refractive index: Na-D line , 20 ° C

Perillaaldehyde is a chemical compound from the group of aldehydes that occurs in two enantiomeric forms. It belongs to the natural product class of monoterpenes .

Occurrence

Caraway seed

Perillaaldehyde occurs naturally in perilla oil and cumin . Both enantiomeric forms generally occur in nature.

properties

( S ) - (-) - Perillaaldehyde is a yellow oily liquid.

use

( S ) - (-) - Perillaaldehyde is used as a starting product for the production of nature-identical substances. Its oxime perillartin (perilla sugar) is 2000 times sweeter than sugar and is used as a sugar substitute in Japan.

toxicology

According to EFSA and the latest evaluations of a study, perillaaldehyde causes DNA damage to the liver. However, "some weaknesses in the historical control data" of the laboratory conducting the studies were also identified.

Individual evidence

  1. ↑ a b c d e f g data sheet (S) - (-) - Perillaldehyde, ≥92% from Sigma-Aldrich , accessed on December 3, 2013 ( PDF ).
  2. ↑ a b c d e Ashutosh Kar: Pharmacognosy And Pharmacobiotechnology . New Age International, 2003, ISBN 81-224-1501-6 , pp. 321 ( limited preview in Google Book search).
  3. ↑ He-ci Yu, Kenichi Kosuna, Megumi Haga: Perilla: The Genus Perilla . CRC Press, 1997, ISBN 1-4398-2271-9 , pp. 129 ( limited preview in Google Book search).
  4. ↑ Robert Ebermann, I. Elmadfa: Textbook food chemistry and nutrition . Springer DE, 2008, ISBN 3-211-49348-4 , pp. 262 ( limited preview in Google Book search).
  5. ↑ a b from Atta-ur-Rahman: Stereoselective Synthesis (Part J) - Atta-ur-Rahman . Elsevier, 1995, ISBN 0-08-054178-X , pp. 230, 251 ( limited preview in Google Book search).
  6. ↑ EFSA: Flavoring substance considered a safety concern