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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 668
実験および物理化学的性質
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
- 外見
- 粉
- 酸解離定数(Pka)
- 2.2 · 2.2, 4.4, 6.7(at 25℃)
- 色
- 白い
- 水溶解度
- 実質的に不溶
- BRN
- 1407295 · 1407295
- 安定性
- 安定していますが、湿気に弱いです。強酸化剤、強塩基、アミン、酸とは相容れない。
- 主な用途
- 磁性ナノワイヤー、免疫測定法、タンパク質分析、染色体同定、サルモネラ菌モソーム、癌の診断、腎臓病、病原体の検出、遺伝子、サルモネラ菌細胞、トキソプラズマ症、酵素による核酸切断、大腸癌の表面分子、癌治療、慢性リンパ性白血病
- InChI
- 1S/C21H11NO5S/c23-12-2-5-16-18(8-12)26-19-9-13(24)3-6-17(19)21(16)15-4-1-11(22-10-28)7-14(15)20(25)27-21/h1-9,23-24H
- InChIKey
- MHMNJMPURVTYEJ-UHFFFAOYSA-N
- SMILES
- Oc1ccc2c(Oc3cc(O)ccc3C24OC(=O)c5cc(ccc45)N=C=S)c1
- CAS データベース
- 3326 · 3326-32-7(CAS DataBase Reference)
- EPAの化学物質情報
- -1 · Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 3',6'-dihydroxy-5-isothiocyanato- (3326-32-7)
化学的性質
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
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
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
毒性情報
Treatment
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
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)
Toxicity Summary
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)
法規制情報
Regulatory Information
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
- safety_code
- 22-45-36/37/39-26-36/37-36
- Hazard Classifications
- Resp. Sens. 1Skin Sens. 1
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
Metabolism/Metabolites
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
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
Used as a fluorescent indicator to probe biological systems and monitor sewage; [Merck Index]
Fluorescein isothiocyanate is used in flow cytometry. (L552)
応用分野
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
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.]
上流・下流製品情報
上流原料
サプライヤー50 社
補足説明
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
関連ノート
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