Rose Bengal Lactone

HCID 69439

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Basic information

CAS: 4159-77-7
Standard SMILES: O=C1OC2(c3cc(I)c(O)c(I)c3Oc3c2cc(I)c(O)c3I)c2c(Cl)c(Cl)c(Cl)c(Cl)c21
InChIKey: IICCLYANAQEHCI-UHFFFAOYSA-N
Molecular formula: C20H4Cl4I4O5
Average molar mass: 973.7 g/mol
Monoisotopic mass: 971.4992

Names & identifiers

Preferred name: Rose Bengal Lactone
IUPAC: 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodospiro[2-benzofuran-3,9'-xanthene]-1-one
English name: Rose bengal lactone
Molecular formula: C20H4Cl4I4O5
Molecular weight: 973.67

Names & synonyms

Rose Bengal lactone4159-77-7Solvent Red 141C.I. Solvent Red 141Bengal Rose B4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodo-3h-spiro[2-benzofuran-1,9'-xanthen]-3-oneUNII-BIU7Q7W2SHBIU7Q7W2SHC.I.45440:1DTXSID0048426ROSE BENGAL ACIDEINECS 223-993-4

Show more names

4’,5’,7’-tetraiodo-droxy-2C.I.Solvent Red 141:C.I.45440:14,5,6,7-Tetrachloro-2’,4’,5’,7’-tetraiodofluoresceinspiro[isobenzofuran-1(3h),9’-[9h]xanthen]-3-one,4,5,6,7-tetrachloro-3’,6’-dihy4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodospiro[2-benzofuran-3,9'-xanthene]-1-one4,5,6,7-Tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodo-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one4,5,6,7-Tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodo-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one4',5',6',7'-Tetrachloro-3,6-dihydroxy-2,4,5,7-tetraiodospiro[9H-xanthene-9,1'(3'H)-isobenzofuran]-3'-one

BLUE 7NSC-457324,5,6,7-tetrachloro-2',4',5',7'-tetraiodofluoresceinRose bengal BSpiro(isobenzofuran-1(3H),9'-(9H)xanthen)-3-one, 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodo-FLUORESCEIN, 4,5,6,7-TETRACHLORO-2',4',5',7'-TETRAIODO-BENZOIC ACID, 2,3,4,5-TETRACHLORO-6-(6-HYDROXY-2,4,5,7-TETRAIODO-3-OXO-3H-XANTHEN-9-YL)-Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodo-

Database identifiers

CAS: 4159-77-7、632-68-8
PubChem CID: 69439
DTXSID: DTXSID0048426
UNII: BIU7Q7W2SH
EC Number: 211-182-8、223-993-4
Nikkaji: J25.139I

Properties

Computed structural properties

XLogP: 8.5
Topological polar surface area: 76 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 5
Rotatable bonds: 0
Heavy atoms: 33
Formal charge: 0
Complexity: 780

Physicochemical properties

Melting point: 280 °C · 280 °C (dec.)(lit.)
storage temp.: room temp
Boiling point: 741.8 · 741.8±60.0 °C(Predicted)
Density: 2.96 · 2.96±0.1 g/cm3(Predicted)
pka: 7.03 · 7.03±0.20(Predicted)
form: powder
color: pink to red
λmax: 557 nm · 557 nm
ε(extinction coefficient): 10000 at · ≥10000 at 317-323nm≥30000 at 516-522nm≥95000 at 554-560nm
Major Application: diagnostic assay manufacturinghematologyhistology
InChI: 1S/C20H4Cl4I4O5/c21-9-7-8(10(22)12(24)11(9)23)20(33-19(7)31)3-1-5(25)15(29)13(27)17(3)32-18-4(20)2-6(26)16(30)14(18)28/h1-2,29-30H
InChIKey: IICCLYANAQEHCI-UHFFFAOYSA-N
SMILES: Oc1c(I)cc2c(Oc3c(I)c(O)c(I)cc3C24OC(=O)c5c(Cl)c(Cl)c(Cl)c(Cl)c45)c1I
FDA UNII: 7 Q7W2SH · BIU7Q7W2SH
EPA Substance Registry System: -1 · Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodo- (4159-77-7)
UNSPSC Code: 12171500 · 12171500
NACRES: 47 · NA.47
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
target organs: Respiratory system
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-37/39
WGK Germany: 3 · 3
TSCA: TSCA listed
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract 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 39 reports by companies from 2 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.

This chemical does not meet GHS hazard criteria for 100% (5 of 5) of all reports.

Hazard information

Regulatory Information · 2 items

Chemical: Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodo-, dipotassium salt

Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodo-, dipotassium salt: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and Categories · 2 items

Skin Irrit. 2 (100%)；Eye Irrit. 2 (100%)；STOT SE 3 (100%)

Not Classified

Regulatory information

Regulatory Information · 2 items

Chemical: Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodo-, dipotassium salt

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
tsca: TSCA listed
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-37/39
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H315-H319-H335
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Uses & manufacturing

General Manufacturing Information · 2 items

Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodo-, potassium salt (1:2): ACTIVE

Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodo-: INACTIVE

Applications · 2 items

DescriptionRose bengal lactone is a potent inhibitor of human metabolism that binds to the proteasome pathway and inhibits the polymerization of tubulin. It has been shown to bind with high affinity to microtubules and inhibit their assembly, which leads to cell death. Rose bengal lactone also binds with high affinity to potassium ion, which may contribute to its anti-cancer effects. This compound has also been found to be an effective inhibitor of goiters in rats by binding with aliphatic hydrocarbons such as cholesterol.

UsesBiological stain; colorant for inks, cellulosics, foods, cosmetics, medicine (diagnostic aid).

Preparation methods

Preparationwill Resorcinol and 4,5,6,7-Tetrachloroisobenzofuran-1,3-dione condensation, The resulting 4,5,6,7 – tetrachloro-fluorescein tetraiodide.