에르고티오네인

에르고티오네인
에르고티오네인 구조식 이미지
카스 번호:
497-30-3
한글명:
에르고티오네인
동의어(한글):
에르고티오네인
상품명:
L-(+)-Ergothioneine
동의어(영문):
ERGOTHIONEINE;ERGOLD;THIONEINE;Ergothionine;2-MERCAPTOHISTIDINE BETAINE;(S)-[1-carboxy-2-(2-mercaptoimidazol-4-yl)ethyl]trimethylammonium hydroxide;(S)-ALPHA-CARBOXY-2,3-DIHYDRO-N,N,N-TRIMETHYL-2-THIOXO-1H-IMIDAZOLE-4-ETHANAMINIUM INNER SALT;Ergotin;NSC 7175;Thiasine
CBNumber:
CB8460398
분자식:
C9H15N3O2S
포뮬러 무게:
229.3
MOL 파일:
497-30-3.mol
MSDS 파일:
SDS

에르고티오네인 속성

녹는점
275-277°C (dec.)
밀도
1.2541 (rough estimate)
굴절률
1.6740 (estimate)
저장 조건
-20°C
용해도
수용성(최대 10mg/ml)
물리적 상태
백색 고체.
색상
흰색 또는 황백색
수소이온지수(pH)
+47^o (c=1 in water)
안정성
제공된 대로 구매일로부터 1년 동안 안정적입니다. 물에 용해된 용액은 -20°C에서 1일 이상 보관할 수 없습니다.
InChI
InChI=1/C9H15N3O2S/c1-12(2,3)7(8(13)14)4-6-5-10-9(15)11-6/h5,7H,4H2,1-3H3,(H2-,10,11,13,14,15)/t7-/s3
InChIKey
SSISHJJTAXXQAX-KPOCXSGKNA-N
SMILES
[N+](C)(C)(C)[C@@H](CC1=CNC(S)=N1)C([O-])=O |&1:4,r|
EPA
1H-Imidazole-4-ethanaminium, .alpha.-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-, inner salt, (.alpha.S)- (497-30-3)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
WGK 독일 3
HS 번호 2933299090
그림문자(GHS): GHS hazard pictograms
신호 어: Warning
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H315 피부에 자극을 일으킴 피부부식성 또는 자극성물질 구분 2 경고 GHS hazard pictograms P264, P280, P302+P352, P321,P332+P313, P362
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 GHS hazard pictograms P264, P280, P305+P351+P338,P337+P313P
H335 호흡 자극성을 일으킬 수 있음 특정 표적장기 독성 - 1회 노출;호흡기계 자극 구분 3 경고 GHS hazard pictograms
예방조치문구:
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P302+P352 피부에 묻으면 다량의 물로 씻으시오.
P304+P340 흡입하면 신선한 공기가 있는 곳으로 옮기고 호흡하기 쉬운 자세로 안정을 취하시오.
NFPA 704
0
2 0

에르고티오네인 C화학적 특성, 용도, 생산

개요

L-(+)-Ergothioneine is a naturally-occurring amino acid derived from histidine via hercynine. Ergothioneine is a stable antioxidant that scavenges and detoxifies free radicals and oxidants, increases intracellular thiol levels, controls nuclear factor-κB activation, and inhibits inflammatory gene expression. In addition, it inhibits the peroxynitrite-dependent nitration of nitrotyrosine, blocks oxidative DNA damage and cell death, and prevents the formation of xanthine and hypoxanthine. Ergothioneine is transported by the organic cation/carnitine transporter 1, which has been linked with autoimmune diseases, including rheumatoid arthritis and Crohn’s disease.

화학적 성질

White Solid

Origin

Ergothioneine was discovered in 1909 by Charles Tanret, a French pharmacist and chemist. Tanret was examining the ergot fungus, which had recently been responsible for destroying crops, and he discovered the compound by using a purification process. The amino acid name ergothioneine originates from this fungus. Though this discovery is relatively recent, scientists speculate that ergothioneine may have originated from ancient earth. Due to its anaerobic nature (it does not require oxygen to function), it may have manifested in the earth's oxygen-free atmosphere more than three billion years ago While ergothioneine is not classified as one of the nine essential amino acids.

benefits

L-(+)-Ergothioneine is a natural antioxidant, which has various physiological functions such as scavenging free radicals, detoxification, maintaining DNA biosynthesis, normal cell growth and cellular immunity.

일반 설명

L-(+)-Ergothioneine (ERG)  is a substance that cannot be synthesized by humans and must be obtained from food. It has cytoprotective and antioxidant properties.

일반 설명

L-(+)-Ergothioneine (ET) is a sulfur-containing amino acid, which is only produced by Actinomycetales bacteria and non-yeast like fungi belonging to the division Basidiomycota and Ascomycota. It was originally isolated from Claviceps purpurea or rye ergot. It is obtained from L-histidine, which is converted into betaine form called hercynine. It is found in both animals and plants, and mammals usually obtain it from their diet, e.g. through mushrooms or oats. It is tautomeric in nature, and in neutral aqueous solution exists in thione form.

Synthesis

L-(+)-Ergothioneine is prepared by the reaction of hercynine. The steps are as follows:
15g of compound was added to 150ml of water, and 15.6g of concentrated hydrochloric acid was added, add 10.9g dibromohydantoin, stir for 20min, add D-cysteine, Continue to stir for 1 hour, add sodium thiosulfate, raise the temperature to 90-100°C, and continue the reaction for 15 hours. After the reaction, cool down and filter, adjust the pH to neutral, desalt, concentrate, crystallize with 5ml of water and 75ml of isopropanol, and dissolve the solid Filter and dry at 70-80°C to obtain 88% ergothioneine product with a yield of 81%.
L-(+)-Ergothioneine synthesis

에르고티오네인 준비 용품 및 원자재

원자재

준비 용품


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