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N-아세틸-D-글루코사민

N-Acetyl-D-Glucosamine

HCID 439174
새 노트새 반응견적 요청하기
인쇄 미리보기
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
7512-17-6
표준 SMILES
CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O
InChIKey
OVRNDRQMDRJTHS-RTRLPJTCSA-N
분자식
C8H15NO6
평균 분자량
221.21 g/mol
단동위원소 질량
221.0899372

개요

N-acetyl-D-glucosamine is the D isomer of N-acetylglucosamine. It has a role as a bacterial metabolite. It is a N-acetyl-D-hexosamine and a N-acetylglucosamine.

이름 및 식별자

우선 이름
N-Acetyl-D-Glucosamine
IUPAC
N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
현지명
N-아세틸-D-글루코사민
영어명
N-Acetyl-D-Glucosamine
분자식
C8H15NO6
분자량
221.21

이름 및 동의어

2-acetamido-2-deoxy-D-glucopyranoseGlcNAc2-Deoxy-2-Acetamido-D-Glucopyranosen-acetyl-glucosamine2-acetamido-2-deoxy-glucose2-Deoxy-2-Acetamido-Glucose2-Acetamido-2-Deoxy-Glucopyranose2-Deoxy-2-Acetamido-Glucopyranose2-acetamido-2-deoxy-glucopyranoside2-Deoxy-2-Acetamido-Glucopyranoside2-acetamido-2-deoxy-D-glucopyranoside2-Deoxy-2-Acetamido-D-Glucopyranoside
이름 더 보기
N-아세틸-D-글루코사민N-아세틸-D-글루코사민(N-ACETYL-D-GLUCOSAMINE)아세틸글루코사민N-ACETYLGLUCOSAMINEacetylglucosamineN-Acetyl-D-glucosaminN-Acetyl-beta-D-glucosamineNADGAcetyl chitin2-Acetamido-D-glucose
2-Acetamido-2-Deoxy-D-Glucose2-Deoxy-2-Acetamido-D-GlucoseD-GlcNAcGlcNAc (SNFG)N-Acetyl-D-GlucosamineSNFG:GlcNAcN-AcetylchitosamineN-Acetyl-D-glucosamine-Agarose

데이터베이스 식별자

CAS
7512-17-6
PubChem CID
439174
DTXSID
DTXSID901045903
ChEMBL
CHEMBL240524
ChEBI
CHEBI:506227
Nikkaji
J35.752I

물성

구조 계산 물성

XLogP
-1.7
극성 표면적
119 Ų
수소 결합 공여자 수
5
수소 결합 수용자 수
6
회전 가능 결합 수
2
무거운 원자 수
15
형식 전하
0
복잡도
235

실험 및 물리화학적 성질

LogP-2.1
Solubility · 2건

167 mg/mL

>33.2 [ug/mL] (The mean of the results at pH 7.4)

Melting Point210 °C
Physical DescriptionSolid
Collision Cross Section · 2건

147.3 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

160.36 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]

물리화학적 성질

녹는점
211 °C · 211 °C (dec.) (lit.)
증기압
8 Pa · 8Pa at 20℃
굴절률
39 to · +39.0 to +42.0 ° (C=1, H2O)
저장 조건
-20 °C · -20°C
용해도
진한 염산, 황산, 인산 및 포름산에 용해됩니다. 물, 묽은 산, 묽은 알칼리, 농축 알칼리 및 유기 용매에 불용성입니다.
끓는 점
636.4 · 636.4±55.0 °C(Predicted)
밀도
1.54 g/cm3 · 1.54 g/cm3
산도 계수 (pKa)
13.04 · 13.04±0.20(Predicted)

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
LZ6651000
HS 번호
29329985
risk_code
36/37/38
hazard_code
Xi
safety_code
24/25-36-26-22
F 고인화성물질
3-10
위험 참고 사항
Irritant
스토리지 클래스
11 - Combustible Solids

화학 및 산업

약리 정보

Tissue LocationsIntestine
Cellular LocationsCytoplasm
Metabolite PathwaysAmino Sugar Metabolism
응용 분야 · 4건

개요N-Acetyl-D-Glucosamine is the N-acetyl derivative of glucosamine.Chemically it is an amide between glucosamine and acetic acid. A single N-acetlyglucosamine moiety linked to serine or threonine residues on nuclear and cytoplasmic proteins -O-GlcNAc, is an ubiquitous post-translational protein modification. O-GlcNAc modified proteins are involved in sensing the nutrient status of the surrounding cellular environment and adjusting the activity of cellular proteins accordingly. O-GlcNAc regulates cellular responses to hormones such as insulin, initiates a protective response to stress, modulates a cell's capacity to grow and divide, and regulates gene transcription. In humans, it exists in skin, cartilage and blood vessel as a component of hyaluronic acid, and bone tissue, cornea and aorta as a component of keratan sulfate. N-Acetyl-D-glucosamine (D-GlcNAc) is a derivitized glucose monomer found in polymers of bacterial cell walls, chitin, hyaluronic acids and various glycans. It is also synthesized in the glycosylation pathway as uridine diphosphate (UDP-GlcNAc), which can then be released following degradation of glycosylated proteins.D-GlcNAc is used to identify, differentiate and characterize N-acetyl-β-D-hexoaminidase(s). It is also used in the treatment of osteoarthritis and inflammatory bowel disease (IBD), including ulcerative colitis and Crohn's disease. Further, it is used as a substrate in sialic acid production, cosmetics and in drug development research.

용도N-Acetyl-D-glucosamine is used in the identification and characterization of N-acetyl-beta-D-hexoaminidase. It is also used in the treatment of osteoarthritis and inflammatory bowel disease (IBD), including ulcerative colitis and Crohn's disease. Further, it is used as a substrate in sialic acid production, cosmetics and in drug development research.

용도N-acetyl-D-Glucosamine (GlcNAc) is a monosaccharide derivative of glucose. It is released by the action of O-GlcNAcase, in mammalian systems from proteins that have been post-translationally modified with O-GlcNAc.D-GlcNAc enhances the proliferation and collagen expression of fibroblasts, reduces hyperpigmentation and is therefore considered a valuable ingredient in cosmetics for improving skin wrinkles and color.Important substrate for the production of sialic acids.Used in multiple other applications in drug development and food supplement, based on a newly described bio-wave model.

관련 반응

38건
반응 기록 만들기
HRID 2686 반응식
HRID 2686반응물로uspto-grants-1998_03
HRID 21346 반응식
HRID 21346반응물로uspto-grants-1995_06
HRID 21347 반응식
HRID 21347반응물로uspto-grants-1995_06
HRID 257307 반응식
HRID 257307생성물로uspto-grants-1993_11
HRID 257720 반응식
HRID 257720반응물로uspto-grants-1993_11
HRID 429740 반응식
HRID 429740생성물로uspto-grants-2001_11
HRID 482209 반응식
HRID 482209반응물로uspto-grants-1998_08
HRID 532103 반응식
HRID 532103반응물로uspto-grants-2014_10
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화합물 노트

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더보기
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물리적 상태
식염수 현탁액
색상
흰색에서 황백색까지
생물학적 소스
crab (red)
수용성
2 O: · H2O: 50 mg/mL 무색 ~ 희미한 노란색 용액, 투명 ~ 매우 약간 흐릿한 용액
Merck
14 · 14,4458
BRN
1727589 · 1727589
안정성
안정적인. 강한 산화제와 호환되지 않습니다.
InChI
1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-,8/m1/s1
InChIKey
OVRNDRQMDRJTHS-ROGOILFBSA-N
SMILES
CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O
LogP
-2.2 at · -2.2 at 23.7℃
EPA
N-Acetylglucosamine (7512-17-6)

화학적 성질

White powder

일반 설명N-Acetyl-D-glucosamine (GlcNAc) is a monosaccharide, derived from glucose and undergoes linear polymerization by (1,4)-β-linkages to form the polymer chitin. It is also a component of heterogenous polysaccharides, such as murein and hyaluronic acid. N-acetylglucosamine exhibits anti-inflammatory properties and is considered as a potential drug in the treatment of osteoarthritis. Its antiarthritic mode of mechanism involves the suppression of IL-1β (Interleuken-1β)-induced NO (nitric oxide), cyclooxygenase-2 (COX-2), and IL-6 production by inhibition of expression of iNOS (inducible nitric oxide synthase) protein and mRNA.Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

상·하류 제품 정보

하류 제품

Benzyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside말토덱스트린

추가 설명

정의ChEBI: N-acetyl-D-glucosamine is the D isomer of N-acetylglucosamine. It has a role as a bacterial metabolite. It is a N-acetylglucosamine and a N-acetyl-D-hexosamine.