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크산틴

Xanthine

HCID 1188
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
69-89-6
표준 SMILES
O=c1[nH]c(=O)c2[nH]cnc2[nH]1
InChIKey
LRFVTYWOQMYALW-UHFFFAOYSA-N
분자식
C5H4N4O2
평균 분자량
152.11 g/mol
단동위원소 질량
152.03342538

개요

9H-xanthine is an oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-9 is protonated. It has a role as a Saccharomyces cerevisiae metabolite. It is a tautomer of a 7H-xanthine.

이름 및 식별자

우선 이름
Xanthine
IUPAC
3,7-dihydropurine-2,6-dione
현지명
크산틴
영어명
Xanthine
분자식
C5H4N4O2
분자량
152.11

이름 및 동의어

xanthine69-89-62,6-Dihydroxypurine2,6-dioxopurineXanthinIsoxanthineXanthic oxidePseudoxanthine1H-Purine-2,6-diol9H-Purine-2,6-diol3,7-Dihydro-1H-purine-2,6-dione1H-Purine-2,6-dione, 3,7-dihydro-
이름 더 보기
크산틴크잔틴잔틴Xan7H-xanthineDioxopurine1H-Purine-2,6(3H,7H)-dione
Purine-2,6-diol3,7-dihydropurine-2,6-dione2,6(1,3)-Purinedion3,9-dihydro-1H-purine-2,6-dione2,6-Dioxo-1,2,3,6-tetrahydropurine1H-Purine-2,6-dione, 3,9-dihydro-9H-Purine-2,6-(1H,3H)-dionePurine-2,6(1H,3H)-dione

데이터베이스 식별자

CAS
69-89-6
PubChem CID
1188
DTXSID
DTXSID4035120
ChEMBL
CHEMBL1424
ChEBI
CHEBI:17712
UNII
1AVZ07U9S7
EC Number
200-718-6
Nikkaji
J2.371J

물성

구조 계산 물성

XLogP
-0.7
극성 표면적
86.9 Ų
수소 결합 공여자 수
3
수소 결합 수용자 수
3
회전 가능 결합 수
0
무거운 원자 수
11
형식 전하
0
복잡도
217

실험 및 물리화학적 성질

Chemical ClassesNitrogen Compounds -> Purines
DrugsPharmaceuticals -> Listed in ZINC15
CosmeticsSkin conditioning
SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy
LogP · 2건

-0.73

-0.73

Solubility0.069 mg/mL at 16 °C; 9.5 mg/mL (sodium salt)
Melting Point> 300 °C
Physical Description · 2건

Solid; [Merck Index] White odorless powder; [Alfa Aesar MSDS]

Solid

Dissociation Constants7.53
Collision Cross Section · 5건

124.36 Ų [M-H]- [CCS Type: DT; Method: stepped-field]

120.6 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

124 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine]

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

안전 및 규제

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

GHS 분류

GHS Classification · 5건

This chemical does not meet GHS hazard criteria for 3.7% (3 of 82) of reports.

Warning

H317 (85.4%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 82 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Regulatory Information · 4건

Chemical: 1H-Purine-2,6-dione, 3,7-dihydro-

1H-Purine-2,6-dione, 3,9-dihydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1H-Purine-2,6-dione, 3,9-dihydro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

REACH registered substance: Purine-2(3H),6(1H)-dione (EC: 200-718-6)

1H-Purine-2,6-dione, 3,7-dihydro-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards Summary · 1건

May cause irritation; [Alfa Aesar MSDS] An irritant that may cause severe eye irritation; May cause skin sensitization; [Sigma-Aldrich MSDS] PubMed search for (69-89-6[EC/RN Number]) AND (allergic or sensitizer or sensitization or dermatitis): no records supporting skin sensitization; [PubMed]

Hazard Classes and CategoriesSkin Sens. 1 (85.4%)

독성 정보

화학 및 산업

약리 정보

Metabolism/Metabolites · 1건

Xanthine is readily converted to uric acid. The enzyme xanthine oxidase makes uric acid from xanthine and hypoxanthine, which in turn are produced from other purines. In humans and higher primates, uric acid is the final oxidation (breakdown) product of purine metabolism and is excreted in urine.

Tissue LocationsBladder
Cellular LocationsCytoplasm
Metabolite PathwaysAdenine phosphoribosyltransferase deficiency (APRT)

용도 및 제조

Uses · 2건

Found in animal organs, yeast, potatoes, coffee beans, and tea; [Merck Index] A purine base found in most body tissues and fluids, certain plants, and some urinary calculi. It is an intermediate in the degradation of adenosine monophosphate to uric acid, being formed by oxidation of hypoxanthine. The methylated xanthine compounds caffeine, theobromine, and theophylline and their derivatives are used in medicine for their bronchodilator effects. (Dorland, 28th ed) [ChemIDplus]

Naturally produced by the body (endogenous).

U.S. Production2023: <50,000 lb
Use ClassificationCosmetics -> Skin conditioning
General Manufacturing Information1H-Purine-2,6-dione, 3,9-dihydro-: ACTIVE
응용 분야 · 2건

용도2,6-Dihydroxypurine was fund in animal organs, yeast, patatoes, coffee beans, tea. 2,6-Dihydroxypurine can be used to relax and widen certain breathing passages of the lungs. It is also found that a large number of derivatives have adenoside receptor antagonist properties.

관련 반응

40건
반응 기록 만들기
HRID 48094 반응식
HRID 48094생성물로uspto-grants-2004_03
HRID 115955 반응식
HRID 115955반응물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 231626 반응식
HRID 231626반응물로uspto-grants-1989_07
HRID 293683 반응식
HRID 293683반응물로Training data from https://doi.org/10.1039/C8SC04228D (8/10)
HRID 377183 반응식
HRID 377183반응물로uspto-grants-2000_02
HRID 377185 반응식
HRID 377185반응물로uspto-grants-2000_02
HRID 429028 반응식
HRID 429028반응물로uspto-grants-2001_11
HRID 482882 반응식
HRID 482882반응물로uspto-grants-1986_03
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122.2 Ų [M-H]-

물리화학적 성질

녹는점
300 °C · 300 °C
끓는 점
274.55 °C · 274.55°C (rough estimate)
밀도
1.5452 · 1.5452 (rough estimate)
증기 밀도
5.3 · 5.3 (vs air)
굴절률
1.85 · 1.8500 (estimate)
저장 조건
Keep in dark place,Sealed in dry,Room Temperature
용해도
4 OH: · NH4OH: 자유롭게 용해됨
산도 계수 (pKa)
9.95 · pKa 9.95 (Uncertain)
물리적 상태
가루
색상
흰색에서 약간 노란색
냄새
냄새 없는
생물학적 소스
synthetic (organic)
수용성
물에 용해됨(0.067g/L).
비열
0.99 J/ · Cp(crystal): 0.99 J/(g·K), at 25℃
Merck
14 · 14,10059
BRN
8733 · 8733
화장품 원료 기능
피부 컨디셔닝
InChI
1S/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11)
InChIKey
LRFVTYWOQMYALW-UHFFFAOYSA-N
SMILES
O=C1NC(=O)c2nc[nH]c2N1
LogP
-0.73 · -0.730
NIST
Xanthine(69-89-6)
EPA
Xanthine (69-89-6)

화학적 성질

White to off-white crystalline powder

Treatment · 1건

Chronic Exposure: Kidney dialysis is usually needed to relieve the symptoms of xanthine toxicity until normal kidney function can be restored. Acute Exposure: EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice.

Health Effects · 1건

Chronically high concentrations of xanthine can lead to health problems such as renal failure and xanthine kidney stones, one of the rarest types of kidney stones. Chronically high levels of xanthine are associated with at least 4 inborn errors of metabolism including: Xanthinuria type I, Xanthuria type II, Molybdenium Cofactor Deficiency, and Xanthinuria.

Exposure RoutesEndogenous, Ingestion, Dermal (contact)
Toxicity SummaryXanthine is a poorly soluble compound. As a result high concentrations of serum xanthine can lead to the formation of kidney stones (xanthine kidney stones) which can, over the long term, induce kidney failure.
Signs and SymptomsMay lead to arthropathy, myopathy, crystal nephropathy, urolithiasis, or renal failure.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
ZD7700000
HS 번호
29335990
risk_code
36-43-36/37/38
hazard_code
Xi
safety_code
36/37-37/39-26
기존화학 물질
KE-10741
스토리지 클래스
11 - Combustible Solids

일반 설명Xanthine is a purine that can be produced in the purine metabolic pathway via different precursors:Guanine deamination by guanine deaminaseHypoxanthine conversion by xanthine oxidoreductase

상·하류 제품 정보

상류 원료

Semicarbazide이미다졸디에틸 카보네이트3-이소부틸-1-메틸삭틴5,6-디아미노피리미딘-2,4-디올황산염4-Amino-2,6-dihydroxy-5-nitrosopyrimidine요산4,5-Diaminouracil하이포크산틴1,3,5-트리아진

하류 제품

카페인6-머캡토퓨린2-ChloroadenineTheobromine8-아미노잔틴2,6-Dichloropurine

추가 설명

정의A poisonous colorless crystalline organic compound that occurs in blood, coffee beans, potatoes, and urine. It is used as a chemical intermediate.