The Vespiary

The Hive => Chemicals & Equipment => Topic started by: Dextrose on September 17, 2002, 11:03:00 AM

Title: Possible Piperonal source?
Post by: Dextrose on September 17, 2002, 11:03:00 AM
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
Title: Yes. Heliotropin = Piperonal
Post by: Organikum on September 17, 2002, 03:20:00 PM
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 (http://l2.espacenet.com/dips/viewer?PN=US2916499&CY=gb&LG=en&DB=EPD)

(1959 to Welsbach Corp.); Holum, J. Org. Chem. 26, 4814 (1961);

Feugeas, Bull. Soc. Chim. France 1964, 1892 (https://www.thevespiary.org/rhodium/Rhodium/pdf/benzodioxole.deriviatives.pdf)

(https://www.thevespiary.org/rhodium/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 (http://www.omikron-online.de/cyberchem/aroinfo/0568-aro.htm)


~ Love is the law, love under will. ~
Title: U.S. pat. 2,916,499: Ozonization of isosafrole to ...
Post by: Rhodium on September 17, 2002, 04:13:00 PM
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.
Title: check your patent number
Post by: jimwig on September 17, 2002, 06:21:00 PM
2,916,499:
Title: Huh?
Post by: Rhodium on September 17, 2002, 06:27:00 PM
Huh?
Title: Maybe, maybe not.
Post by: terbium on September 17, 2002, 07:38:00 PM
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


Title: Worth a try?
Post by: Dextrose on September 18, 2002, 08:51:00 AM
Would it be worth a try to order a liter and (blindly) try to distill it out?
// Dex
Title: US2916499
Post by: jimwig on September 19, 2002, 05:38:00 PM
US2916499
                 
                  Process for producing aromatic carbonyl compounds and peroxide compounds

maybe i misunderstood but

maybe somebody changed something. i dunno.
Title: Jimwig: The patent number is correct, the ...
Post by: Rhodium on September 19, 2002, 07:41:00 PM
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.