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Rosolic acid, also known as Aurin, is a red crystalline or powdery substance derived from phenol or carbolic acid. It is soluble in alcohol and ether but insoluble in water. Rosolic acid possesses a range of chemical properties and applications, making it a versatile compound in various industries.

603-45-2

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603-45-2 Usage

Uses

Used in Antioxidative Stress and DNA Fragmentation Inhibition:
Rosolic acid is used as an anti-oxidative stress agent and an inhibitor of DNA fragmentation, playing a crucial role in maintaining cellular integrity and preventing damage at the molecular level.
Used in Coloring and Photography Industry:
Rosolic acid serves as a red coloring medium in the coloring and photography industry. Its nonactinic property makes it safe for use in darkrooms, windows, and doorways. Additionally, it is mixed with water-soluble gums and applied as an antihalation layer on the backs of collodion and silver bromide gelatin plates.
Used as a pH Indicator:
Rosolic acid is utilized as a pH indicator, with a range from 5.0 to 6.8. This application is essential in various chemical and biological processes that require precise pH control.
Used in Dye Manufacturing:
Rosolic acid acts as an intermediate in the manufacturing of dyes, contributing to the production of a wide range of colored compounds used in various industries.
Used in Bacterial Isolation:
Rosolic acid finds application in the selective isolation of coliform bacteria, which is vital in the fields of microbiology and environmental science for the detection and analysis of specific bacterial strains.

Purification Methods

It forms green crystals with a metallic luster, but the colour depends on the solvent used. When recrystallised from brine (saturated aqueous NaCl) acidified with HCl, it forms red needles, but when recrystallised from EtO/AcOH, the crystals have a beetle iridescent green colour. It has been recrystallised from Me2CO (although it dissolves slowly), methyl ethyl ketone, 80-95% AcOH and from AcOH/*C6H6. An aqueous KOH solution is golden yellow, and a 70% H2SO4 solution is deep red in colour. An alternative purification is to dissolve this triphenylmethane dye in 1.5% of aqueous NH3, filter, and heat to 70-80o, then acidify with dilute AcOH by adding it slowly with vigorous stirring, whereby the aurin separates as a brick-red powder or as purplish crystals depending on the temperature and period of heating. Filter off the solid, wash it with H2O and a little dilute AcOH, then H2O again. Stir this solid with Et2O to remove any ketones and allow it to stand overnight in the Et2O, then filter and dry it in air then in a vacuum. [Gomberg & Snow J Am Chem Soc 47 202 1925, Baines & Driver J Chem Soc 123 1216 1923, UV: Burawoy Chem Ber 64 462 1941, Beilstein 8 IV 2646.]

Check Digit Verification of cas no

The CAS Registry Mumber 603-45-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,0 and 3 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 603-45:
(5*6)+(4*0)+(3*3)+(2*4)+(1*5)=52
52 % 10 = 2
So 603-45-2 is a valid CAS Registry Number.
InChI:InChI=1/C19H14O3/c20-16-7-1-13(2-8-16)19(14-3-9-17(21)10-4-14)15-5-11-18(22)12-6-15/h1-12,20-21H

603-45-2 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
  • Packaging
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  • Detail
  • Alfa Aesar

  • (B21737)  Rosolic acid   

  • 603-45-2

  • 25g

  • 619.0CNY

  • Detail
  • Alfa Aesar

  • (B21737)  Rosolic acid   

  • 603-45-2

  • 100g

  • 1087.0CNY

  • Detail
  • Aldrich

  • (861324)  p-Rosolic acid  Dye content 85 %

  • 603-45-2

  • 861324-25G

  • 971.10CNY

  • Detail
  • Aldrich

  • (861324)  p-Rosolic acid  Dye content 85 %

  • 603-45-2

  • 861324-100G

  • 3,253.77CNY

  • Detail

603-45-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-[bis(4-hydroxyphenyl)methylidene]cyclohexa-2,5-dien-1-one

1.2 Other means of identification

Product number -
Other names Aurin No. 555

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:603-45-2 SDS

603-45-2Synthetic route

tetrachloromethane
56-23-5

tetrachloromethane

phenol
108-95-2

phenol

A

1-trifluoromethoxybenzene
456-55-3

1-trifluoromethoxybenzene

B

aurin
603-45-2

aurin

Conditions
ConditionsYield
With hydrogen fluorideA 31%
B 69%
tetrachloromethane
56-23-5

tetrachloromethane

2-(trifluoromethoxy)phenol
32858-93-8

2-(trifluoromethoxy)phenol

A

1,2-bis-trifluoromethoxybenzene
129644-61-7

1,2-bis-trifluoromethoxybenzene

B

aurin
603-45-2

aurin

Conditions
ConditionsYield
With hydrogen fluorideA 48%
B 45%
tetrachloromethane
56-23-5

tetrachloromethane

2-monochlorophenol
95-57-8

2-monochlorophenol

A

o-chloro-α,α,α-trifluoromethoxybenzene
450-96-4

o-chloro-α,α,α-trifluoromethoxybenzene

B

aurin
603-45-2

aurin

Conditions
ConditionsYield
With hydrogen fluorideA 35%
B 47%
o-chloro-α,α,α-trifluoromethoxybenzene
450-96-4

o-chloro-α,α,α-trifluoromethoxybenzene

aurin
603-45-2

aurin

Conditions
ConditionsYield
With hydrogen fluoride; tantalum pentachloride31%
1-trifluoromethoxybenzene
456-55-3

1-trifluoromethoxybenzene

aurin
603-45-2

aurin

Conditions
ConditionsYield
With hydrogen fluoride; tantalum pentachloride at 140℃; for 4h; Cooling with ice;25%
1-chloro-4-(trifluoromethoxy)benzene
461-81-4

1-chloro-4-(trifluoromethoxy)benzene

aurin
603-45-2

aurin

Conditions
ConditionsYield
With hydrogen fluoride; tantalum pentachloride20%
1,4-bis-trifluoromethoxybenzene
660-36-6

1,4-bis-trifluoromethoxybenzene

aurin
603-45-2

aurin

Conditions
ConditionsYield
With hydrogen fluoride; tantalum pentachloride20%
1,2-bis-trifluoromethoxybenzene
129644-61-7

1,2-bis-trifluoromethoxybenzene

aurin
603-45-2

aurin

Conditions
ConditionsYield
With hydrogen fluoride; tantalum pentachloride15%
tetrachloromethane
56-23-5

tetrachloromethane

2-Phenoxyphenol
2417-10-9

2-Phenoxyphenol

A

4-hydroxy-9H-xanthen-9-one
14686-63-6

4-hydroxy-9H-xanthen-9-one

B

aurin
603-45-2

aurin

Conditions
ConditionsYield
With hydrogen fluorideA 10%
B 7%
tetrachloromethane
56-23-5

tetrachloromethane

potassium phenolate
100-67-4

potassium phenolate

aurin
603-45-2

aurin

Conditions
ConditionsYield
at 170℃; analoge Reaktionen finden mit Kalium-o-kresolat und Kalium-m-kresolat statt;
at 170 - 190℃;
tetrachloromethane
56-23-5

tetrachloromethane

sodium phenoxide
139-02-6

sodium phenoxide

aurin
603-45-2

aurin

Conditions
ConditionsYield
at 170 - 190℃;
4,4'-Dihydroxybenzophenone
611-99-4

4,4'-Dihydroxybenzophenone

aurin
603-45-2

aurin

Conditions
ConditionsYield
With phosphorus trichloride Erhitzen des Reaktionsproduktes mit Phenol und etwas Schwefelsaeure auf 140grad;
oxalic acid
144-62-7

oxalic acid

phenol
108-95-2

phenol

aurin
603-45-2

aurin

Conditions
ConditionsYield
With sulfuric acid
With sulfuric acid
tetrachloromethane
56-23-5

tetrachloromethane

phenol
108-95-2

phenol

aurin
603-45-2

aurin

Conditions
ConditionsYield
With zinc(II) chloride at 135℃;
at 150℃;
With aluminium trichloride at 140 - 160℃; Behandlung des Reaktionsproduktes mit Wasser;
With zinc(II) chloride at 140 - 160℃; Behandlung des Reaktionsproduktes mit Wasser;
formaldehyd
50-00-0

formaldehyd

phenol
108-95-2

phenol

aurin
603-45-2

aurin

Conditions
ConditionsYield
With hydrogenchloride
formic acid
64-18-6

formic acid

phenol
108-95-2

phenol

aurin
603-45-2

aurin

Conditions
ConditionsYield
With zinc(II) chloride at 120℃;
p-cresol
106-44-5

p-cresol

phenol
108-95-2

phenol

aurin
603-45-2

aurin

Conditions
ConditionsYield
With sodium hydroxide; sodium dichromate at 180℃; unter Druck;
carbon tetrabromide
558-13-4

carbon tetrabromide

phenol
108-95-2

phenol

aurin
603-45-2

aurin

Conditions
ConditionsYield
With zinc(II) chloride
With potassium hydroxide; copper
chloropicrin
76-06-2

chloropicrin

phenol
108-95-2

phenol

aurin
603-45-2

aurin

Conditions
ConditionsYield
With aluminium trichloride Auskochen des Reaktionsproduktes mit verd.Salzsaeure;
With sodium hydroxide at 50 - 60℃; dann bei Siedetemperatur;
bis-(4-hydroxyphenyl)methane
620-92-8

bis-(4-hydroxyphenyl)methane

phenol
108-95-2

phenol

aurin
603-45-2

aurin

Conditions
ConditionsYield
With sulfuric acid; sodium nitrite
tetrachloromethane
56-23-5

tetrachloromethane

phenol
108-95-2

phenol

trichloroacetic acid
76-03-9

trichloroacetic acid

A

aurin
603-45-2

aurin

B

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

C

salicylaldehyde
90-02-8

salicylaldehyde

diethyl ether
60-29-7

diethyl ether

phenol
108-95-2

phenol

trichloroacetic acid
76-03-9

trichloroacetic acid

aurin
603-45-2

aurin

Conditions
ConditionsYield
at 190℃; Reaktion von Natrium-phenolat;
furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

phenol
108-95-2

phenol

trichloroacetic acid
76-03-9

trichloroacetic acid

A

aurin
603-45-2

aurin

B

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

C

salicylaldehyde
90-02-8

salicylaldehyde

diethyl ether
60-29-7

diethyl ether

sodium phenoxide
139-02-6

sodium phenoxide

trichloroacetic acid
76-03-9

trichloroacetic acid

aurin
603-45-2

aurin

Conditions
ConditionsYield
at 190℃;
sodium phenoxide
139-02-6

sodium phenoxide

trichloroacetic acid
76-03-9

trichloroacetic acid

aurin
603-45-2

aurin

Conditions
ConditionsYield
With diethyl ether at 190℃;
tetrachloromethane
56-23-5

tetrachloromethane

aluminium trichloride
7446-70-0

aluminium trichloride

phenol
108-95-2

phenol

aurin
603-45-2

aurin

Conditions
ConditionsYield
at 140 - 160℃; im Autoklaven und anschl. Auskochen mit Wasser;
4,4'-Dihydroxybenzophenone
611-99-4

4,4'-Dihydroxybenzophenone

sulfuric acid
7664-93-9

sulfuric acid

phosphorus trichloride
7719-12-2, 52843-90-0

phosphorus trichloride

phenol
108-95-2

phenol

aurin
603-45-2

aurin

tetrachloromethane
56-23-5

tetrachloromethane

p-cresol
106-44-5

p-cresol

water
7732-18-5

water

phenol
108-95-2

phenol

Na2Cr2O7

Na2Cr2O7

aurin
603-45-2

aurin

Conditions
ConditionsYield
at 180℃; unter Druck;
p-cresol
106-44-5

p-cresol

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

phenol
108-95-2

phenol

Na2Cr2O7

Na2Cr2O7

aurin
603-45-2

aurin

Conditions
ConditionsYield
at 180℃; unter Druck;
sulfuric acid
7664-93-9

sulfuric acid

bis-(4-hydroxyphenyl)methane
620-92-8

bis-(4-hydroxyphenyl)methane

phenol
108-95-2

phenol

NaNO2

NaNO2

aurin
603-45-2

aurin

aurin
603-45-2

aurin

4,4',4''-methylidynetrisphenol
603-44-1

4,4',4''-methylidynetrisphenol

Conditions
ConditionsYield
With sodium tetrahydroborate; acetic acid In ethanol76%
aurin
603-45-2

aurin

benzoyl chloride
98-88-4

benzoyl chloride

4,4',4''-tris(benzoyloxy)tritylcarbinol
86610-67-5

4,4',4''-tris(benzoyloxy)tritylcarbinol

Conditions
ConditionsYield
In pyridine for 1h; Heating;58%
With 2,3-Dimethylaniline at 60℃; nachf. Behandlung des Reaktionsprodukts mit verd. Salzsaeure und Natronlauge;
aurin
603-45-2

aurin

4-methoxy-benzoyl chloride
100-07-2

4-methoxy-benzoyl chloride

tris<4-(p-anisoyloxy)phenyl>methanol
118161-45-8

tris<4-(p-anisoyloxy)phenyl>methanol

Conditions
ConditionsYield
With pyridine at 80 - 90℃; for 1.5h;44%
ethanol
64-17-5

ethanol

aurin
603-45-2

aurin

propargyl bromide
106-96-7

propargyl bromide

ethyl tris<4-(2-propynoxy)phenyl>methyl ether
142044-06-2

ethyl tris<4-(2-propynoxy)phenyl>methyl ether

Conditions
ConditionsYield
With potassium carbonate for 12h; Heating;44%
aurin
603-45-2

aurin

4-(4,4'-dimethoxy-benzhydrylidene)-cyclohexa-2,5-dienone
184865-84-7

4-(4,4'-dimethoxy-benzhydrylidene)-cyclohexa-2,5-dienone

Conditions
ConditionsYield
With diethyl ether
ethanol
64-17-5

ethanol

aurin
603-45-2

aurin

4-(4,4'-dihydroxy-benzhydrylidene)-cyclohexa-2,5-dienone; dihydrochloride, compound with ethanol

4-(4,4'-dihydroxy-benzhydrylidene)-cyclohexa-2,5-dienone; dihydrochloride, compound with ethanol

Conditions
ConditionsYield
With hydrogenchloride
aurin
603-45-2

aurin

4,4'-Dihydroxybenzophenone
611-99-4

4,4'-Dihydroxybenzophenone

Conditions
ConditionsYield
With sodium hydroxide; air
aurin
603-45-2

aurin

pararosaniline
467-62-9

pararosaniline

Conditions
ConditionsYield
With ammonium hydroxide at 120℃;
aurin
603-45-2

aurin

4,4'-dihydroxy-3,5,3',5'-tetraiodo-benzophenone
15198-16-0

4,4'-dihydroxy-3,5,3',5'-tetraiodo-benzophenone

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; iodine; potassium iodide
aurin
603-45-2

aurin

4,4',4''-triaminotriphenylmethane
548-61-8

4,4',4''-triaminotriphenylmethane

Conditions
ConditionsYield
With ethanol; ammonia at 150℃;
aurin
603-45-2

aurin

2,6-dibromo-4-(3,5,3',5'-tetrabromo-4,4'-dihydroxy-benzhydrylidene)-cyclohexa-2,5-dienone

2,6-dibromo-4-(3,5,3',5'-tetrabromo-4,4'-dihydroxy-benzhydrylidene)-cyclohexa-2,5-dienone

Conditions
ConditionsYield
With bromine; acetic acid
aurin
603-45-2

aurin

2,6-dichloro-4-(3,5,3',5'-tetrachloro-4,4'-dihydroxy-benzhydrylidene)-cyclohexa-2,5-dienone

2,6-dichloro-4-(3,5,3',5'-tetrachloro-4,4'-dihydroxy-benzhydrylidene)-cyclohexa-2,5-dienone

Conditions
ConditionsYield
With sulfuryl dichloride; iron(III) chloride; acetic acid
aurin
603-45-2

aurin

4-(4,4'-bis-phosphonooxy-benzhydrylidene)-cyclohexa-2,5-dienone

4-(4,4'-bis-phosphonooxy-benzhydrylidene)-cyclohexa-2,5-dienone

Conditions
ConditionsYield
With pyridine; chloroform; trichlorophosphate beim Behandeln des Reaktionsprodukts mit H2O;
aurin
603-45-2

aurin

4-(4,4'-dihydroxy-benzhydrylidene)-cyclohexa-2,5-dienone; sulfate

4-(4,4'-dihydroxy-benzhydrylidene)-cyclohexa-2,5-dienone; sulfate

Conditions
ConditionsYield
With sulfuric acid; acetic acid
aurin
603-45-2

aurin

4-(4,4'-dihydroxy-benzhydrylidene)-cyclohexa-2,5-dienone; sulfate

4-(4,4'-dihydroxy-benzhydrylidene)-cyclohexa-2,5-dienone; sulfate

Conditions
ConditionsYield
With ethanol; sulfuric acid
aurin
603-45-2

aurin

tris-(4-hydroxy-phenyl)-methanesulfinic acid ; sodium salt

tris-(4-hydroxy-phenyl)-methanesulfinic acid ; sodium salt

Conditions
ConditionsYield
With sodium hydroxide; sodium dithionite
aurin
603-45-2

aurin

4-(4,4'-dihydroxy-benzhydrylidene)-1-hydroxy-cyclohexa-2,5-dienesulfonic acid ; sodium-salt

4-(4,4'-dihydroxy-benzhydrylidene)-1-hydroxy-cyclohexa-2,5-dienesulfonic acid ; sodium-salt

Conditions
ConditionsYield
With water; sodium hydrogensulfite
aurin
603-45-2

aurin

4-(4,4'-dihydroxy-benzhydrylidene)-cyclohexa-2,5-dienone; sulfite

4-(4,4'-dihydroxy-benzhydrylidene)-cyclohexa-2,5-dienone; sulfite

Conditions
ConditionsYield
With ethanol; sulfur dioxide; water

603-45-2Related news

Degradation of ROSOLIC ACID (cas 603-45-2) by advanced oxidation processes: ozonation vs. solar photocatalysis07/16/2019

Rosolic acid has been used as model compound to check the efficiency of different advanced oxidation processes in the abatement of dyestuffs having triphenylmethane structure. Ozone is very effective; even at low flows (17 × 10−3 min−1 for an ozone flow of 0.2 g h−1) important degradation rates...detailed

603-45-2Relevant academic research and scientific papers

Single label comparative hybridization

-

, (2015/01/06)

The present invention provides methods of detecting and mapping chromosomal or genetic abnormalities associated with various diseases or with predisposition to various diseases, or to detecting the phenomena of large scale copy number variants. In particular, the present invention provides advanced methods of performing array-based comparative hybridization that allow reproducibility between samples and enhanced sensitivity by using the same detectable label for both test sample and reference sample nucleic acids. Invention methods are useful for the detection or diagnosis of particular disease conditions such as cancer, and detecting predisposition to cancer based on detection of chromosomal or genetic abnormalities and gene expression level. Invention methods are also useful for the detection or diagnosis of hereditary genetic disorders or predisposition thereto, especially in prenatal samples. Moreover, invention methods are also useful for the detection or diagnosis of de novo genetic aberrations associated with post-natal developmental abnormalities.

Lability of the trifluoromethyl group of trifluoromethoxybenzenes under HF/Lewis acid conditions

Belter, Randolph K.

scheme or table, p. 1302 - 1307 (2011/02/22)

The trifluoromethyl functionality of trifluoromethoxybenzenes (trifluoromethyl phenyl ethers) becomes labile under HF/Lewis acid conditions. Substrates with an unsubstituted para-position shed their -CF3 groups while performing a Friedel-Crafts reaction upon another substrate molecule's trifluoromethoxy group to generate p-rosolic acids. Substrates that had blocking groups at the para-positions reacted ortho. The electron donating substituents methoxy and phenoxy interfered with the formation of rosolic acids.

Substractive single label comparative hybridization

-

, (2009/04/24)

Provided are methods of determining differences between nucleic acids in a test sample and a reference sample. In certain embodiments the methods are used for detecting and mapping chromosomal or genetic abnormalities associated with various diseases or with predisposition to various diseases, or to detecting the phenomena of large scale copy number variants. In particular, provided are advanced methods of performing array-based comparative hybridization that allow reproducibility between samples and enhanced sensitivity by using the same detectable label for both test sample and reference sample nucleic acids. Invention methods are useful for the detection or diagnosis of particular disease conditions such as cancer, and detecting predisposition to cancer based on detection of chromosomal or genetic abnormalities and gene expression level. Invention methods are also useful for the detection or diagnosis of hereditary genetic disorders or predisposition thereto, especially in prenatal samples. Moreover, invention methods are also useful for the detection or diagnosis of de novo genetic aberrations associated with post-natal developmental abnormalities.

Multiconstituent liquid lgG and IgM calibrators

-

, (2008/06/13)

A serum in which are dissolved at least two heterologous antibodies, which are independently IgG or IgM and which specifically bind to different antigens, serves as a calibrator for multi-analyte immunoassays.

Oligonucleotides comprising a molecular switch

-

, (2008/06/13)

This invention relates to oligonucleotides comprising a molecular switch which may exist in an “open” or “closed” position. The molecular switch portion of the probe is particularly sensitive to the identity of sequences complementary to the molecular switch. Oligonucleotides containing a molecular switch are applicable to all kinds of hybridization processes. Due to the sensitivity of the switch domain of the oligonucleotide, probes containing a molecular switch are particularly useful in the identification of single point mismatches. More specifically, a portion, but not all, of the oligonucleotide becomes unbound from a mismatched target. The invention further relates to methods of using said oligonucleotides for research reagents, and clinical diagnostics. An exemplary oligonucleotide comprises a first hybridizable domain, a second bridging block domain, and a third binding domain.

Dual resonance energy transfer nucleic acid probes

-

, (2008/06/13)

Dual nucleic acid probes with resonance energy transfer moieties are provided. In particular, fluorescent or luminescent resonance energy transfer moieties are provided on hairpin stem-loop molecular beacon probes that hybridize sufficiently near each other on a subject nucleic acid, e.g. mRNA, to generate an observable interaction. The invention also provides lanthanide chelate luminescent resonance energy transfer moieties on linear and stem-loop probes that hybridize sufficiently near each other on a subject nucleic acid to generate an observable interaction. The invention thereby provides detectable signals for rapid, specific and sensitive hybridization determination in vivo. The probes are used in methods of detection of nucleic acid target hybridization for the identification and quantification of tissue and cell-specific gene expression levels, including response to external stimuli, such as drug candidates, and genetic variations associated with disease, such as cancer.

Nucleic acid amplification oligonucleotides with molecular energy transfer labels and methods based thereon

-

, (2008/06/13)

The present invention provides labeled nucleic acid amplification oligonucleotides, which can be linear or hairpin primers or blocking oligonucleotides. The oligonucleotides of the invention are labeled with donor and/or acceptor moieties of molecular energy transfer pairs. The moieties can be fluorophores, such that fluorescent energy emitted by the donor is absorbed by the acceptor. The acceptor may be a fluorophore that fluoresces at a wavelength different from the donor moiety, or it may be a quencher. The oligonucleotides of the invention are configured so that a donor moiety and an acceptor moiety are incorporated into the amplification product. The invention also provides methods and kits for directly detecting amplification products employing the nucleic acid amplification primers. When labeled linear primers are used, treatment with exonuclease or by using specific temperature eliminates the need for separation of unincorporated primers. This "closed-tube" format greatly reduces the possibility of carryover contamination with amplification products, provides for high throughput of samples, and may be totally automated.

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