Daminozide

Daminozide

Names
IUPAC name 4-(2,2-Dimethylhydrazinyl)-4-oxobutanoic acid
Other names N-(Dimethylamino)succinamic acid; Butanedioic acid mono (2,2-dimethyl hydrazine); Succinic acid 2,2-dimethyl hydrazide
Identifiers
CAS Number	1596-84-5 Y
3D model (Jmol)	Interactive image
Beilstein Reference	1863230
ChemSpider	14593 Y
ECHA InfoCard	100.014.988
EC Number	216-485-9
KEGG	C10996 Y
MeSH	daminozide
PubChem	15331
RTECS number	WM9625000
UNII	F6KF33M5UB Y
InChI InChI=1S/C6H12N2O3/c1-8(2)7-5(9)3-4-6(10)11/h3-4H2,1-2H3,(H,7,9)(H,10,11) Y Key: NOQGZXFMHARMLW-UHFFFAOYSA-N Y
SMILES CN(C)NC(=O)CCC(O)=O
Properties
Chemical formula	C6H12N2O3
Molar mass	160.17 g·mol−1
Appearance	White crystals
Melting point	159.24 °C; 318.63 °F; 432.39 K
Hazards
Lethal dose or concentration (LD, LC):
LD50 (median dose)	>1,600 mg kg−1(dermal, rabbit) 8,400 mg kg−1(oral, rat)
Related compounds
Related alkanoic acids	Octopine
Related compounds	1,2-Dimethylhydrazine Biurea Bis-tris propane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Daminozide — also known as Alar, Kylar, B-NINE, DMASA, SADH, or B 995 — is a plant growth regulator, a chemical sprayed on fruit to regulate their growth, make their harvest easier, and keep apples from falling off the trees before they are ripe. This makes sure they are red and firm for storage. Alar was first approved for use in the U.S. in 1963, it was primarily used on apples until 1989 when it was voluntarily withdrawn by the manufacturer after the U.S. Environmental Protection Agency proposed banning it based on concerns about cancer risks to consumers.

It has been produced in the U.S. by the Uniroyal Chemical Company, Inc, (now integrated into the Chemtura Corporation) which registered daminozide for use on fruits intended for human consumption in 1963. In addition to apples and ornamentals, it was also registered for use on cherries, peaches, pears, Concord grapes, tomato transplants and peanut vines. On fruit trees, daminozide affects flow-bud initiation, fruit-set maturity, fruit firmness and coloring, preharvest drop and market quality of fruit at harvest and during storage. In 1989, it became illegal to use daminozide on food crops in the US, but it is still allowed for use on non-food crops like ornamentals.

In 1985, the EPA conducted studies on Alar on mice and hamsters and proposed to ban the substance's use on food crops. The proposal was submitted to the Scientific Advisory Panel (SAP) which concluded that the tests were inadequate to determine how carcinogenic the tested substances were. Later it was discovered that at least one of the SAP members had a financial connection to Uniroyal and others had financial ties to the chemical industry.

The next year, the EPA retracted its proposed ban and required farmers to reduce the use of Alar by 50%. The American Academy of Pediatrics urged EPA to ban daminozide and some manufacturers and supermarket chains announced they would not accept Alar-treated apples.