Document ID: EPA-HQ-OPP-2009-0121-0005
Agency: epa
Document Type: Supporting & Related Material
Title: 
Posted Date: 2009-03-25T04:00Z

UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

 		     WASHINGTON, D.C. 20460

 ADVANCE \d61 			ICE OF PREVENTION,

OFFICE OF PESTICIDES AND TOXIC SUBSTANCES        

MEMORANDUM

DATE:		February 23, 2009

SUBJECT:	Registration Review: Product Chemistry Data Review for
Capsaicin and Related Capsaicinoids   

Registration Review Case: 	4018

PC Code:					070701,070706,070707

CAS Number:				404-86-4, 19408-84-5, 28789-35-7

Chemical Class: 				Biochemical

 

FROM:		Nina Simeonova, Chemist, NOWCC-SEE      /s/	

Biopesticides & Pollution Prevention Division (7511P)

TO:			Chris Pfeifer, Regulatory Action Leader

Biochemical Pesticides Branch

Biopesticides & Pollution Prevention Division (7511P) 

ACTION REQUESTED

The available information for Product Chemistry of the currently
registered products, containing the active ingredient Capsaicin and
Related Capsaicinoids is assessed according to the preliminary work plan
for Registration Review of Capsaicin Case # 4018.

Introduction

Capsaicin is used as active ingredient in pesticide formulation to repel
mammals, insects and birds by non-toxic mode of action. The first
product of this type is a dog repellent registered in 1962. 

EPA published the R.E.D., Case 4018, for Capsaicin in June 1992.  

Currently Capsaicin is the active ingredient in 41 active and 9 pending
registrations alone or in combination with other biochemical (Oil of
Mustard, Garlic Oil, Oil of Black Pepper, Oleoresin of Black Pepper,
Putrescent Whole Eggs) or conventional (Butanethiol) active ingredients.
 Four products registered as bear repellents are regulated by RD. 

Capsaicin (PC Code 070701, CASRN 404-86-4) is the major pungent
repelling ingredient in the products under review. It is not registered
separately as TGAI. It is introduced in the formulations through two
different types of source materials. The older registrations use hot
sauces, sold primarily as food flavoring additives. The newer
registrations use the industrially produced extracts of ripe dried hot
peppers like Capsicum Frutescens or Capsicum Annum (botanical family
Solanaceae, genus Capsicum). The technical name of the extracts is
Oleoresin Capsicum identified in OPPIN by PC Code 070704 and CAS #
8023-77-6.  The currently registered repellent products contain
Oleoresin of Capsicum with varying content of Capsaicin and different
total composition depending on the specificity of the extraction
process. Aquaresin of Capsicum, which is soluble both in oils and in
water, is requested as alternate source of Capsaicin by some producers
of pesticides. 

Oleoresin Capsicum is regulated as direct addition to food by FDA
(21CFR§73.345, 21CFR§180.10 and 21CFR§180.20). 

None of the different types of Oleoresin Capsicum used in the currently
active EPA’s products is registered for manufacturing use only. 

The currently registered pesticides with active ingredient Capsaicin are
marketed as sprays, emulsifiable concentrates, soluble concentrates,
ready-to-use solutions or granules. 

Capsaicin is cleared for food use under 40CFR§180.1165.

Description of the active ingredient

The precise description of the active ingredient takes into account that
Capsaicin is always co-extracted from the hot peppers with at least 3
also pungent structurally similar compounds. Together they form the
complex active ingredient in Oleoresin of Capsicum. Capsaicin is
identified in OPPIN by PC Code 070701 and CASRN 404-86-4.  PC Code
070706 is assigned to Dihydrocapsaicin (CARN 19408-84-5).
Nordihydrocapsaicin (CASRN 28789-35-7) has PC Code 070707. Capsaicin and
Dihydrocapsaicin contribute to 80-90 % of the total amount of the
Capsaicinoids in Oleoresin of Capsicum, Capsaicin being in largest
amount and with strongest pungency.   

The chemical identification of the major Capsaicinoids in Oleoresin of
Capsicum follows: 

Capsaicin

Chemical structure

 

Common Name:						Capsaicin

Chemical Name and Synonyms:		N-[(4-Hydroxy-3-Methoxyphenyl)-Methyl]-8-

                                                            
Methyl-6E-Nonenamide(9CI);

                                                           
8-Methyl-N-Vanillyl- 6(E)-Nonenamide

                                                     

PC Code                                              070701

CAS Number:							404-86-4

Molecular Weight:					305.4

Molecular Formula:					C18H27NO3

Physical form:							White crystalline powder

Melting Point:							65 °C

Boiling Point                                       210-220 °C (0.01Hg)

Absorption maximums:				227 nm, 281 nm

Solubility:							      Practically insoluble in water, soluble in
Ethanol, 

                                                             Ether,
Benzene, Chloroform 

Dihydrocapsaicin

Chemical Structure

 

Common Name:						Dihydrocapsaicin

Chemical Name and Synonyms:		N-[(4-Hydroxy-3-Methoxyphenyl)-Methyl]-8-

                                                            
Methyl-Nonanamide(9CI);

                                                           
8-Methyl-N-Vanillyl-Nonanamide

PC Code:								070706

CAS Number:						      19408-84-5

Molecular Weight:					307.4

Molecular Formula:					C18H29NO3

Melting Point                                       65.5-65-8 °C

Other Physical Characteristics of Dihydrocapsaicin are not found in the
open literature. 

Nordihydrocapsaicin

Chemical Structure

 

Common Name:						Nordihydrocapsaicin

Chemical Name and Synonyms:		7-Methyl-N-Vanillyl-Octaneamide

PC Code:								070707

CAS Number:						     28789-35-7

Molecular Weight:					293.4

Molecular Formula:					C17H27NO3

Melting point:							60-61 °C 

Other Physical Characteristics of Nordihydrocapsaicin are not found in
the open literature. 

Note to the RAL:

1. Because all the reviewed products are end-use, what Physical and
Chemical Characteristics are required depend on the specific physical
form and composition of a product.

2. The review found some trivial deficiencies like some un-updated CSFs
(after transfer) and some labels missing the qualification of the
ingredient statement. 

 

cc: N. Simeonova, C. Pfeifer. BPPD Chron File.

      N. Simeonova, PY-S. 02/23/2009.

Capsaicin and Related Capsaicinoids

404-86-4, 19408-84-5, 28789-35-7                                        
                         Case 4018    

 PAGE   

 PAGE   2 

Capsaicin and Related Capsaicinoids

404-86-4, 19408-84-5, 28789-35-7                                        
                         Case 4018