Agaritine
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Agaritine
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CAS No:
2757-90-6
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Formula:
C12H17N3O4
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Chemical Name:
Agaritine
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Synonyms:
L-Glutamic acid,5-[2-[4-(hydroxymethyl)phenyl]hydrazide];Glutamic acid,5-[2-(α-hydroxy-p-tolyl)hydrazide],L-;Agaritine;β-N-[γ-L(+)-Glutamyl]-4-hydroxymethylphenylhydrazine
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CAS No:
Description
PHYSICAL DESCRIPTION: Colorless glistening crystals. (NTP, 1992)
Agaritine appears as colorless glistening crystals. (NTP, 1992)
Agaritine appears as colorless glistening crystals. (NTP, 1992)|Agaritine is a carbohydrazide, a L-glutamic acid derivative, a member of benzyl alcohols and a non-proteinogenic L-alpha-amino acid. It is a tautomer of an agaritine zwitterion.
Agaritine Basic Attributes
267.283
267.28
UX8Y7QVP8M
DTXSID9020661
GLISTENING CRYSTALS FROM DILUTE ALCOHOL
Characteristics
125
-2.8
Agaritine appears as colorless glistening crystals. (NTP, 1992)
1.2145 (rough estimate)
205-209 °C (decomp)
VERY FREELY SOL IN WATER; PRACTICALLY INSOL IN USUAL ANHYDROUS ORG SOLVENTS
D25 +7° (c = 0.8)
PKA IN WATER: 3.4 & 8.86
DECOMPOSES @ 205-209 °C|Stable in solid state; sensitive to oxidation; rapidly oxidized by a variety of oxidants; hydrolysed by hydrochloric acid to L-glutamic acid|Agaritine is destroyed by moist heat
Water soluble.
Acids, Carboxylic
An amino acid derivative. Toxic gases are formed by mixing AGARITINE with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. Flammable gases are formed by mixing agaritine with alkali metals.
Safety Information
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
The flash point of this chemical has not been determined, but it is probably combustible. (NTP, 1992)
This compound is not very flammable but any fire involving this compound may produce dangerous vapors. You should evacuate the area. All firefighters should wear full-body protective clothing and use self-contained breathing apparatuses. You should extinguish any fires involving this chemical with a dry chemical, carbon dioxide, foam, or halon extinguisher. (NTP, 1992)
SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. RECOMMENDED GLOVE MATERIALS: Permeation data indicate that polyvinyl chloride gloves may provide protection to contact with this compound. Polyvinyl chloride over latex gloves is recommended. However, if this chemical makes direct contact with your gloves remove them at once. (NTP, 1992)
Toxicity
OCCURS NATURALLY IN THE MUSHROOM AQARICUS BISPORUS|The yield of agaritine from Agaricus bisporus is about 0.4 g/kg fresh weight(1).
The estimated total US consumption of Agaricus bisporus was approximately 163 million kg in 1975 and increased to 213 million kg during the 1979-1980 season(1). The yield of agaritine from Agaricus bisporus is about 0.4 g/kg fresh weight(1).
Drug Information
Sporophores of Agaricus bisporus contain gamma-glutamyl transferase, which cleaves agaratine to L-glutamate and 4-(hydroxymethyl)phenylhydrazine. This hydrolysis may also be catalyzed by enzymes found in mammalian gut.|Two enzymic pathways in Agaricus bisporus generate the 4-(hydroxymethyl)benzenediazonium ion from agaritine: (1) conversion of agaritine to 4-(hydroxymethyl)penylhydrazine and further oxidation to the respective diazonium ion. (2) conversion of agaritine to 4-(hydroxymethyl)benzenediazonium ion, without formation of the hydrazine intermediate. These enzyme systems appear to be responsible for the occurrence of the 4-(hydroxymethyl)benzenediazonium ion at a level of 0.6 ppm in the mushroom.
ACUTE/CHRONIC HAZARDS: Very Toxic. Hazardous decomposition products. Experimental carcinogen. (NTP, 1992)
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
agaritine
Agaritine Use and Manufacturing
Occurs naturally in mushrooms...isolated from the cultivated, commonly eaten mushroom Agaricus bisporus by extraction with water or methanol and isolation from the extract by one of several methods
(1977) NOT PRODUCED COMMERCIALLY IN US|(1983) NOT PRODUCED COMMERCIALLY IN US
CONSTITUENT OF COMMERCIAL, EDIBLE MUSHROOM AGARICUS BISPORUS (LANGE) SING. (PSALLIOTA HORTENSIS COOKE VARIETY BISPORA), AGARICACEAE (AGARICALES). ISOLATION & STRUCTURE: LEVENBURG, FED PROC 19, 6 (1960); J AM CHEM SOC 83, 503 (1961); DANIELS ET AL, AM CHEM SOC 83, 3333 (1961).|The mushroom Agaricus bisporus, in which agaritine occurs, is commonly cultivated and eaten...
Methods have been reported for the analysis of agaritine in Agaricus bisporus by ion-exchange column chromatography, high performance thin-layer chromatography, paper chromatography and electrophoresis (Levenberg B; J Biol Chem 239: 2267-73 (1964); Chiarlo B et al; Fitoterapia 50: 111-3 (1979); Oka Y et al; Agaricus Bisporus J Nutr Sci Vitaminol 27: 253-62 (1964))
Computed Properties
Molecular Weight:267.28
XLogP3:-2.8
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:7
Exact Mass:267.12190603
Monoisotopic Mass:267.12190603
Topological Polar Surface Area:125
Heavy Atom Count:19
Complexity:303
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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