フルオレセインイソチオシアナート (I型)

Fluorescein 5-isothiocyanate

HCID 18730CAS 3326-32-7

基本情報

標準SMILES
O=C1OC2(c3ccc(O)cc3Oc3cc(O)ccc32)c2ccc(N=C=S)cc21
InChIKey
MHMNJMPURVTYEJ-UHFFFAOYSA-N
分子式
C21H11NO5S
平均分子量
389.4 g/mol
単同位体質量
389.03579362

名称と識別子

優先名称
Fluorescein 5-isothiocyanate
IUPAC
3',6'-dihydroxy-6-isothiocyanatospiro[2-benzofuran-3,9'-xanthene]-1-one
現地名
フルオレセインイソチオシアナート (I型)
英語名
Fluorescein 5-isothiocyanate
分子式
C21H11NO5S
分子量
389.38

名称と別名

3326-32-75-FITCFLUORESCEIN-5-ISOTHIOCYANATEfluorescein 5-isothiocyanate5-isothiocyanatofluoresceinSpiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 3',6'-dihydroxy-5-isothiocyanato-CHEBI:37918DTXSID80892440I223NX31W9Spiro(isobenzofuran-1(3H),9'-(9H)xanthen)-3-one, 3',6'-dihydroxy-5-isothiocyanato-5 IsothiocyanatofluoresceinFluorescein 5 isothiocyanate
名称をさらに表示
フルオレセインイソチオシアナート (I型)3,6-ジヒドロキシ-5'-イソチオシアナトスピロ[9H-キサンテン-9,1'(3'H)-イソベンゾフラン]-3'-オンフルオレセインイソチオシアナート5-イソチオシアナトフルオレセインフルオレッセインイソチオシアナート3,6-ジヒドロキシ-3'-オキソスピロ[9H-キサンテン-9,1'(3'H)-イソベンゾフラン]-5'-イルイソチオシアナート5-(イソチオシアナト)-3',6'-ジヒドロキシスピロ[イソベンゾフラン-1(3H),9'-[9H]キサンテン]-3-オンフルオレセイン5'-イソチオシアナート3',6'-ジヒドロキシ-5-イソチオシアナトスピロ[イソベンゾフラン-1(3H),9'-[9H]キサンテン]-3-オン5-イソチオシアン酸フルオレセインイソチオシアン酸5-フルオレセイン,アイソマーIフルオレセイン5-イソチオシアナート (アイソマーI)5-イソチオシアナトフルオレセイン (アイソマーI)フルオレセインイソチオシアナート (アイソマーI)5‐イソチオシアン酸フルオレセインイソチオシアン酸5‐フルオレセイン,アイソマーIフルオレセイン-5-イソチオシアネートイソチオシアン酸フルオレセイン, イソマーI型5-イソチオシアン酸フルオレセイン, ISOMER 1イソチオシアン酸フルオレセイン, イソマー I 型Fluorescein isothiocyanate isomer5-FLUORESCEIN ISOTHIOCYANATEFluorescein isothiocyanate isomer I, tech gradeFITC-IFluorescein isothiocyanate IFluorescein isothiocyanate,Isomer I(FITC)
Fluorescein 5 isothiocyanate HydrochlorideHydrochloride, Fluorescein-5-isothiocyanateRefChem:140896DTXCID3029368222-042-0FITCFluorescein isothiocyanate isomer I3',6'-dihydroxy-5-isothiocyanato-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one

データベース識別子

CAS
3326-32-7
PubChem CID
18730
DTXSID
DTXSID80892440
ChEMBL
CHEMBL516313
ChEBI
CHEBI:37918
UNII
I223NX31W9
EC Number
222-042-0
Nikkaji
J205.408F

物性

構造計算による物性

XLogP
4.8
極性表面積
120 Ų
水素結合供与体数
2
水素結合受容体数
7
回転可能結合数
1
重原子数
28

実験および物理化学的性質

Physical DescriptionOrange solid; [Merck Index] Orange powder; [Alfa Aesar MSDS]

物理化学的性質

融点
360 °C · >360 °C(lit.)
沸点
708.6 · 708.6±60.0 °C(Predicted)
比重(密度)
1.3423 · 1.3423 (rough estimate)
屈折率
1.506 · 1.5060 (estimate)
貯蔵温度
2 · 2-8°C
溶解性
DMSO、エタノール、メタノール、DMF、アセトンに微溶
化学的性質 · 1 件

化学的特性Fluorescein isothiocyanate(3326-32-7) is an orange-yellow crystal that is hygroscopic. It can be combined with various antibody proteins, and the combined antibody does not lose its specificity for binding to a certain antigen, and still has strong green fluorescence in alkaline solution, precipitates out after adding acid, and the fluorescence disappears. It is slightly soluble in acetone and ether and petroleum ether.

安全と法規制

GHS分類

GHS Classification · 5 件

Danger

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin];H334 (100%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]

P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 169 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

危険有害性情報

Regulatory Information · 2 件

Chemical: Spiro[isobenzofuran-1(3H),9'-(9H)xanthen]-3-one, 3',6'-dihydroxy-5-isothiocyanato-

Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 3',6'-dihydroxy-5-isothiocyanato-: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryCauses cutaneous sensitization (experimental) and effects on inflammation in 3-day intermittent dermal studies of mice; [RTECS] May cause irritation; May cause skin and respiratory sensitization; [Alfa Aesar MSDS]
Hazard Classes and CategoriesSkin Sens. 1 (100%);Resp. Sens. 1 (100%)

毒性情報

Treatment · 1 件

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. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Health Effects · 1 件

Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97)

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Exposure RoutesOral (L96) ; inhalation (L96) ; dermal (L96)
Toxicity Summary · 1 件

Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)

Signs and SymptomsCyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (L96, L97)

法規制情報

Regulatory Information · 2 件

Chemical: Spiro[isobenzofuran-1(3H),9'-(9H)xanthen]-3-one, 3',6'-dihydroxy-5-isothiocyanato-

Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 3',6'-dihydroxy-5-isothiocyanato-: Does not have an individual approval but may be used under an appropriate group standard

安全データ

F
10
wgk
3
tsca
TSCA listed
hs_code
29329990
risk_code
42/43-36/37/38-22
hazard_code
Xn,Xi

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

Cyanide is rapidly alsorbed through oral, inhalation, and dermal routes and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)

MeSH Pharmacological Classification · 1 件

Chemicals that emit light after excitation by light. The wave length of the emitted light is usually longer than that of the incident light. Fluorochromes are substances that cause fluorescence in other substances, i.e., dyes used to mark or label other compounds with fluorescent tags.

用途と製造

Uses · 2 件

Used as a fluorescent indicator to probe biological systems and monitor sewage; [Merck Index]

Fluorescein isothiocyanate is used in flow cytometry. (L552)

General Manufacturing InformationSpiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 3',6'-dihydroxy-5-isothiocyanato-: ACTIVE
応用分野 · 2 件

説明Fluorescein 5-isothiocyanate (5-FITC) is an isomer of fluorescein isothiocyanate (FITC), which is commonly used as a mixture of the 5- and 6-isothiocyanate isomers. It reacts with amine and thiol groups to form conjugates with proteins, lipids, and other molecules for detection by a variety of fluorescent-based applications. 5-FITC displays excitation/emission maxima of 494/519 nm, respectively.

一般的な説明Fluorescein isothiocyanate (FITC) is yellow-orange in color with an absorption maximum at 495nm. Upon excitation, it emits a yellow-green color with an emission maximum at 525nm.It is widely used to attach a fluorescent label to proteins via the amine group. The isothiocyanate group reacts with amino terminal and primary amines in proteins. It has been used for the labeling of proteins including antibodies and lectins.Fluorescein isothiocyanate isomer I has been proposed as a contact sensitizer.

調製方法 · 1 件

純化方法It is made from the pure 5-amino isomer. Purify it by dissolving it in boiling Me2CO, filtering and adding pet ether (b 60-70o) until it becomes turbid. If an oil separates, then decant it and add more pet ether to the supernatant and cool. Orange-yellow crystals separate, collect and dry them in vacuo. It should give one spot on TLC (silica gel) in EtOAc/pyridine/AcOH (50:1:1) and in Me2NCHO/CHCl3/28% NH4OH (10:5:4). IR (Me2SO): 2110 (NCS) and 1760 (C=O) cm-1. The max 1HNMR spectra in Me2CO-d6 of the 5-and 6-isomers are distinctly different for the protons in the *benzene ring; the UV in phosphate buffer pH 8.0 shows a at ~490nm. [Sinsheimer et al. Anal Biochem 57 2271974, McKinney et al. Anal Biochem 7 74 1964, Beilstein 19 III/IV 4337.]

サプライヤー50 社

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
補足説明 · 1 件

定義ChEBI: Fluorescein 5-isothiocyanate is the 5-isomer of fluorescein isothiocyanate. Acts as a fluorescent probe capable of being conjugated to tissue and proteins; used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.

関連反応

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