基本情報
- CAS
3301-79-9- 標準SMILES
O=C(O)c1ccc2c(c1)C1(OC2=O)c2ccc(O)cc2Oc2cc(O)ccc21- InChIKey
BZTDTCNHAFUJOG-UHFFFAOYSA-N- 分子式
- C21H12O7
- 平均分子量
- 376.3 g/mol
- 単同位体質量
- 376.05830272
概要
6-carboxyfluorescein is a monocarboxylic acid. It is functionally related to a fluorescein (lactone form).
名称と識別子
- 優先名称
- 6-Carboxyfluorescein
- IUPAC
- 3',6'-dihydroxy-1-oxospiro[2-benzofuran-3,9'-xanthene]-5-carboxylic acid
- 現地名
- 3',6'-ジヒドロキシ-3-オキソスピロ[イソベンゾフラン-1(3H),9'-[9H]キサンテン]-6-カルボン酸
- 英語名
- 6-Carboxyfluorescein
- 分子式
- C21H12O7
- 分子量
- 376.32
名称と別名
6-Carboxyfluorescein3301-79-96-FAMJHJ853P6SMCHEBI:39073DTXSID6062965Spiro(isobenzofuran-1(3H),9'-(9H)xanthene)-6-carboxylic acid, 3',6'-dihydroxy-3-oxo-Spiro[isobenzofuran-1(3H),9'-[9H]xanthene]-6-carboxylic acid, 3',6'-dihydroxy-3-oxo-3',6'-Dihydroxy-3-oxospiro(isobenzofuran-1(3H),9'-(9H)xanthene)-6-carboxylic acid3',6'-Dihydroxy-3-oxospiro[isobenzofuran-1(3H),9'-[9H]xanthene]-6-carboxylic acidRefChem:104358DTXCID5038624
名称をさらに表示
3-オキソ-3',6'-ジヒドロキシ-1,3-ジヒドロスピロ[イソベンゾフラン-1,9'-[9H]キサンテン]-6-カルボン酸カルボキシフルオレセイン3',6'-ジヒドロキシ-3-オキソスピロ[イソベンゾフラン-1(3H),9'-[9H]キサンテン]-6-カルボン酸6-カルボキシフルオレセイン6-カルボキシフルオレスセイン6-カルボキシフルオレセイン水和物6-カルボキシフルオレセイン [6-FAM]6-カルボキシフルオレセイン HYDRATE6-FAM (6-カルボキシフルオレセイン)3′,6′-ジヒドロキシ-3-オキソスピロ[イソベンゾフラン-1(3H),9′-[9H]キサンテン]-6-カルボン酸3',6'-ジヒドロキシ-3-オキソ-3H-スピロ[2-ベンゾフラン-1,9'-キサンテン]-6-カルボン酸3-オキソ-3′,6′-ジヒドロキシ-1,3-ジヒドロスピロ[イソベンゾフラン-1,9′-[9H]キサンテン]-6-カルボン酸
物性
構造計算による物性
- XLogP
- 2.9
- 極性表面積
- 113 Ų
- 水素結合供与体数
- 3
- 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
- 637
物理化学的性質
- 融点
- 300 °C · >300 °C(lit.)
- 沸点
- 736.4 · 736.4±60.0 °C(Predicted)
- 比重(密度)
- 1.73 · 1.73±0.1 g/cm3(Predicted)
- 貯蔵温度
- 2 · Sealed in dry,2-8°C
- 溶解性
- DMSO：可溶
- 酸解離定数(Pka)
- 3.3 · 3.3, 4.6, 6.4, 7.0(at 25℃)
- 外見
- 個体
- 色
- 黄色からオレンジ
- BRN
- 54341 · 54341
- 主な用途
- 5 · 血液がん、非胃疾患の診断、遺伝子組み換え小麦の検出、染色体、遺伝子発現、核酸、A型肝炎ウイルス、鳥インフルエンザウイルスH5型およびH5N1型、SARSウイルス、単純ヘルペスウイルス
- InChI
- 1S/C21H12O7/c22-11-2-5-14-17(8-11)27-18-9-12(23)3-6-15(18)21(14)16-7-10(19(24)25)1-4-13(16)20(26)28-21/h1-9,22-23H,(H,24,25)
- InChIKey
- BZTDTCNHAFUJOG-UHFFFAOYSA-N
- SMILES
- OC(=O)c1ccc2C(=O)OC3(c4ccc(O)cc4Oc5cc(O)ccc35)c2c1
- CAS データベース
- 3301 · 3301-79-9(CAS DataBase Reference)
- EPAの化学物質情報
- -1 · Spiro[isobenzofuran-1(3H),9'-[9H]xanthene]-6-carboxylic acid, 3',6'-dihydroxy-3-oxo- (3301-79-9)
化学的性質
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
Warning
H315 (95.2%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Hazard Classes and CategoriesSkin Irrit. 2 (95.2%)
安全データ
- F
- 10-21
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 3204 90 00
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26-36/37
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
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
General Manufacturing InformationSpiro[isobenzofuran-1(3H),9'-[9H]xanthene]-6-carboxylic acid, 3',6'-dihydroxy-3-oxo-: ACTIVE
応用分野
使用6-Carboxyfluorescein (6-FAM) is derivative of fluorescein giving stable derivative upon conjugation with biopolymers.It has been used to check the plasma membrane integrity in sperm cells. The single isomer, 6-FAM, contains a carboxylic acid that can be used to react with primary amines via carbodiimide activation of the carboxylic acid. Commercially available FAM is a mixture of two isomers, 5-FAM and 6-FAM, and the correct name is 5(6)-carboxyfluorescein.
調製方法
製造方法1,2,4-Benzenetricarboxylic anhydride (also called 4- carboxyphthalic anhydride, 25.0 g, 0.13 mol) was added to a solution of 1,3-dihydroxybenzene (also called resorcinol, 28.6 g, 0.26 mol) in methane sulfonic acid (1M). An air condenser was attached to the flask and the reaction was heated at 85 oC in an open vessel for 24 h. After cooling to room temperature, the reaction mixture was poured into 7 volumes of ice/water. An orange-yellow precipitate formed; this was collected by filtration and dried in an oven at 200 oC. This residue was recrystallized two times from methanol/hexane to give 1.0 g of 6- carboxyfluorescein methanesulfonic acid adduct preferentially crystallizes from MeOH/hexanes. The mother liquors from this procedure were collected, the solvent was removed in vacuo, and the residues were recrystallized two times from ethanol/hexanes to give 3.2 g of 5-carboxyfluorescein methanesulfonic acid adduct preferentially crystallizes from EtOH/hexanes. Finally, the mother liquors from this experiment were combined, evaporated to dryness, and recrystallized two times from methanol/hexanes to give another 3.0 g of 6-carboxyfluorescein methanesulfonic acid adduct preferentially crystallizes from MeOH/hexanes, making a total yield of 4.0 g, 40 %. Careful dropwise addition of conc. HCl(aq) to solutions of these methanesulfonic esters preferentially crystallizes from EtOH/hexanes and preferentially crystallizes from MeOH/hexanes in 4M sodium hydroxide gave 5-carboxyfluorescein and 6-carboxyfluorescein, respectively in near quantitative yield.
関連反応
33 件
化合物ノート
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