Dextrose (Newbee)
09-17-02 11:03
No 357332
      Possible Piperonal source?  Bookmark   

SWIM noticed that Piperonal is called Heliotropin in the flavoring industry... Could it be possible that this is the major component of the readily available Oil of Heliotrope ?

SWIM was just wondering, couldn't find any analysis data anywhere...

// Dex
 
 
 
 
    Organikum
(Hive Bee)
09-17-02 15:20
No 357429
      Yes. Heliotropin = Piperonal  Bookmark   

from MERCK INDEX:

Title: Piperonal.
CAS Registry number: [120-57-0]
CAS name(s): 1,3-Benzodioxole-5-carboxaldehyde Additional name(s): 3,4-(methylenedioxy)benzaldehyde; heliotropin ; piperonyl al dehyde; dioxymethyleneprotocatechuic aldehyde
Molecular formula: C 8 H 6 O 3
Molecular weight: 150.13.
Percent Composition: C 64.00%, H 4.03%, O 31.97%.

Literature references: Prepn: Blair, Patent US2916499 (1959 to Welsbach Corp.); Holum, J. Org. Chem. 26, 4814 (1961); Feugeas, Bull. Soc. Chim. France 1964, 1892 (../rhodium/pdf /benzodioxole.deriviatives.pdf). Toxicity: Hagan et al., Toxicol. Appl. Pharmacol. 7, 18 (1965).

Properties: Colorless, lustrous crystals, mp 37degrees . Heliotrope odor. bp approximately263degrees ; bp 0.5 88degrees . Sol in 500 parts water; freely sol in alcohol, ether. Keep in cool place protected from light. LD 50 orally in rats: 2700 mg/kg (Hagan).
 
Boiling point: bp approximately 263degrees; bp 0.5 88degrees
Melting Point: 37degrees
USE: In perfumery, in cherry and vanilla flavors, in organic syntheses.
THERAP CAT: Has been used as pediculicide.



50g cost ~11, it is heavily watched and regulated!
ORGY

for german speaking bees:

more information on chemistry and all (very good) at:

http://www.omikron-online.de/cyberchem/aroinfo/0568-aro.htm

~ Love is the law, love under will. ~
 
 
 
 
    Rhodium
(Chief Bee)
09-17-02 16:13
No 357444
      U.S. pat. 2,916,499: Ozonization of isosafrole to ...  Bookmark   

U.S. pat. 2,916,499: Ozonization of isosafrole to give piperonal in 93% yield.
J. Org. Chem. 26, 4814 (1961): Oxidation of piperonylalcohol to piperonal in 85% yield using CrO3 in Pyridine.
 
 
 
 
    jimwig
(Stranger)
09-17-02 18:21
No 357518
      check your patent number  Bookmark   

2,916,499:
 
 
 
 
    Rhodium
(Chief Bee)
09-17-02 18:27
No 357520
      Huh?  Bookmark   

Huh?
 
 
 
 
    terbium
(Old P2P Cook)
09-17-02 19:38
No 357537
      Maybe, maybe not.  Bookmark   

Oil of heliotrope may or may not contain piperonal. Most Oil of Heliotrope will be compounded rather than being from a single natural source so the composition will depend on the fragrance chemist who determined the formula.

Here is a heliotrope compound formula from Perfumes, Cosmetics & Soaps, Volume 2 by W.A. Poucher.

 

  20  Geraniol, Java
  20  Sweet orange
 250  Heliotropin
  20  Anisic aldehyde
  10  Rose otto
  10  Musk xylene
  20  Peru balsam
 150  Vanillin
 500  Diethyl phthalate
------
1000

 
 
 
 
    Dextrose
(Newbee)
09-18-02 08:51
No 357679
      Worth a try?  Bookmark   

Would it be worth a try to order a liter and (blindly) try to distill it out?

// Dex
 
 
 
 
    jimwig
(Stranger)
09-19-02 17:38
No 358305
      US2916499  Bookmark   

US2916499
                 
                  Process for producing aromatic carbonyl compounds and peroxide compounds

maybe i misunderstood but

maybe somebody changed something. i dunno.
 
 
 
 
    Rhodium
(Chief Bee)
09-19-02 19:41
No 358366
      Jimwig: The patent number is correct, the ...  Bookmark   

Jimwig: The patent number is correct, the synthesis of piperonal from isosafrole is mentioned in the middle of column three, page two of the patent.