Aurin

HCID 5100CAS 603-45-2
Substructure searchFind similar structures

Basic information

Standard SMILES
O=C1C=CC(=C(c2ccc(O)cc2)c2ccc(O)cc2)C=C1
InChIKey
FYEHYMARPSSOBO-UHFFFAOYSA-N
Molecular formula
C19H14O3
Average molar mass
290.3 g/mol
Monoisotopic mass
290.09429431

Overview

Aurin is a diarylmethane.

Names & identifiers

Preferred name
Aurin
IUPAC
4-[bis(4-hydroxyphenyl)methylidene]cyclohexa-2,5-dien-1-one
English name
ROSOLIC ACID
Molecular formula
C19H14O3
Molecular weight
290.31

Names & synonyms

Aurin603-45-2CorallinAurine4,4'-DihydroxyfuchsoneAurin No. 555C.I. 438002,5-Cyclohexadien-1-one, 4-[bis(4-hydroxyphenyl)methylene]-4-[bis(4-hydroxyphenyl)methylene]cyclohexa-2,5-dien-1-one85N4AK3JAUDTXSID2022387NSC-7805
Show more names
P-ROSOLIC ACIDRosoLCI 43800AURIN GRNsc 7805Aurin 555Rosolic aci
4-(Bis(4-hydroxyphenyl)methylene)cyclohexa-2,5-dien-1-one4-(Bis(p-hydroxyphenyl)methylene)cyclohexa-2,5-dien-1-one2,5-Cyclohexadien-1-one, 4-(bis(4-hydroxyphenyl)methylene)-4(bis(p-hydroxyphenyl)methylene)-2,5-cyclohexadien-1-oneRefChem:115651DTXCID002387210-041-8rosolic acid

Database identifiers

CAS
603-45-2
PubChem CID
5100
DTXSID
DTXSID2022387
ChEMBL
CHEMBL210868
ChEBI
CHEBI:34544
UNII
85N4AK3JAU
EC Number
210-041-8
Nikkaji
J9.443I

Properties

Computed structural properties

XLogP
3.9
Topological polar surface area
57.5 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
2
Heavy atoms
22

Experimental & physicochemical properties

Chemical ClassesDyes -> Di- and Triaryl Dyes
Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionDeep red solid; Technical product may be yellowish-brown with a dark green metallic fracture; [Merck Index] Dark red powder; [Sigma-Aldrich MSDS]
Collision Cross Section169.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
309 °C · 309°C (decompose)
Boiling point
372.4 °C · 372.4°C (rough estimate)
Density
1.2497 · 1.2497 (rough estimate)
refractive index
1.42 · 1.4200 (estimate)
storage temp.
Store at room temperature.
solubility
Practically insoluble in water, benzene; freely soluble in ethanol

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): 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 49 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 3 items

Chemical: 2,5-Cyclohexadien-1-one, 4-[bis(4-hydroxyphenyl)methylene]-

PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.

Aurin: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Hazards SummaryA moderate irritant; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
hs_code
29145090
risk_code
36/37/38-36/38
Signal word
Warning

Chemistry & industry

Uses & manufacturing

UsesUsed as a dye intermediate; [Merck Index]
General Manufacturing Information2,5-Cyclohexadien-1-one, 4-[bis(4-hydroxyphenyl)methylene]-: ACTIVE
Applications · 3 items

Usesactivates heme oxygenase, anti-oxidative stress, inhibits DNA fragmentation

UsesA red coloring medium made from phenol or carbolic acid. It is soluble in alcohol and ether but insoluble in water. When fabrics were steeped in this solution, the color was nonactinic and therefore safe for darkrooms, windows, and doorways. Aurin was also mixed with water-soluble gums and brushed on the backs of collodion and silver bromide gelatin plates as an antihalation layer.

UsesRosolic acid is used as a pH indicator in the range from 5.0 to 6.8. It acts as an intermediate in the manufacturing dyes. It is involved in the activation of heme oxygenase and in the inhibition of DNA fragmentation. It finds application in the selective isolation of coliform bacteria.

Upstream & downstream products

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [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]
湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
上海康朗生物科技有限公司021-61998208 18217752821 · [email protected]

Additional notes

DefinitionChEBI: Aurin is a diarylmethane.

Related reactions

0 records
New reaction record

No reaction records under the current filter.

Linked notes

Loading…