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518-82-1 Usage

Physical and chemical properties

Emodin, also known by the Chemical name 1, 3, 8-trihydroxy-6-methyl-anthraquinone with a molecular formula of C15H10O5 and a molecular weight of 270.24, exists in the form of free emodin or emodin glycosides in rhizomes and roots of Rheum palmatum L, Rheum officinale Baill, and Rheum tanguticum Maxim. ex Balf. in the family Polygonaceae. In a form of orange-yellow crystals of melting point of 256-257℃ that can sublimate under a vacuum of 1,600 Pa, the compound is soluble in ethanol, sodium hydroxide, sodium carbonate and aqueous ammonia, slightly soluble in ether, chloroform, carbon tetrachloride and benzene, and almost insoluble in water. Its form as emodin triacetate is yellow crystals of melting point of 197℃, and the form of emodin 3-methyl ether (also known as physcion) is dark-red needle crystals of melting point of 207 ℃. The compound can be obtained by chemical synthesis or by extraction from plants. Aloe-emodin is one of the main components of aloe essential oil, present in the form of aloe-emodin in aloe, or present in the form of glycosides in rhubarb, senna and aloe.

Chemical properties

Orange needles of melting point of 256-257℃ (259-260℃); soluble in alcohol, slightly soluble in ether, chloroform and benzene, and insoluble in water. The solution color would become cherry red when it is dissolved in aqueous caustic solutions, aqueous solution of sodium carbonate or ammonia solution.

Uses

Different sources of media describe the Uses of 518-82-1 differently. You can refer to the following data:
1. 1. The product can be used as a laxative. As it is susceptible to oxidative damage within the body, its diarrhea activity is actually very weak. However, it can be compounded with glucose to form a glycoside with diarrhea activity. Both emodin-1-O-β-D-glucoside and emodin-8-O-β-D-glucoside are glycosides formed through combination of emodin and glucose.? The only different between the two are the binding sites.? The two glycosides coexist in Radix et Rhizoma Rhei. 2. intermediate;health products material.
2. Occurs mostly as the rhamnoside (see Frangulin) in rhubarb root. Cathartic.
3. antibacterial, antineoplastic, cathartic, tyrosine kinase inhibitor
4. Emodin has been used:to investigate its regulatory mechanisms on lipopolysaccharide (LPS)-induced inflammatory injury in myocarditisas a reference standard for the development and validation of high performance liquid chromatography (HPLC)-photodiode array (PDA) assay methodto inhibit Tau aggregationfor direct binding assay

Radix et Rhizoma Rhei

Radix et Rhizoma Rhei is the dry root or rhizome of Rheum palmatum L, Rheum officinale Baill, and Rheum tanguticum Maxim. ex Balf. in the genus Rheum of the family Polygonaceae. Rheum tanguticum Maxim. ex Balf has slender pinnate leaves with three deep lobes and dense inflorescence branches, often erect, clinging to the stem, which are the main difference of it from Rheum palmatum L. The main difference between Rheum tanguticum Maxim. ex Balf. and the other two species mentioned above are its lobed leaves with big serrate or broadly triangular margin, large and yellow-white flowers, oval-shaped flower buds and patulous branches. There are about 60 Rheum species all over the world, of which about 50 are in China. Morphological Characteristics: herbaceous perennial about two meters high. Rhizomes and roots are fleshy and yellowish-brown in color. The stem is erect, smooth, hairless and hollow. The basal leaf has a fleshy, long and sturdy petiole, about as long as the leaf blade. The leaf blade is broadly ovate or nearly round in shape, up to 40 cm in diameter, palmate-cleft with three to five (or to seven) lobes and each lobe sometimes also palmate-cleft or serrate. The leaf base is slightly heart-shaped. The stem leaf is small, shortly stalked. The ocrea is membranous and densely pubescent. Habitat and distribution: Grow in mountain areas, forest margins or grassland, wild or cultivated and distributed in Shaanxi, southeastern Gansu, Qinghai, western Sichuan, northwestern Yunnan and Eastern Tibet. Cultivation: suitable for growing in places with cool and moist climate and with deep soil layer that contains humus-rich sandy loam or calcareous loam, rather than growing in cold places with high temperature and humidity. Harvest: harvest during September to October, select plants that have grown more than three years, dig up the rhizomes and roots, remove the leaves, stems, rootlets, scrape the bark and buds, and then dried in air or in an oven, or sliced and dried. Figure 1 is an image of the Radix et Rhizoma Rhei

Chemical constituents

There have been more than 130 compounds isolated and characterized from a variety species of Rheum, including anthraquinones and anthraquinone glycosides, anthrones, bianthrones and bianthrone glycosides, stilbenes and stilbene glycosides, gallate, naphthalene derivatives, chromanones and chromanone glycosides, banzylethylketone, tannins and so on. Among them the anthraquinones are the most important and representative ingredients. Free anthraquinones mainly include rhein, emodin, physcion, aloe-emodin, and chrysophanol. And anthraquinone glycosides mainly include chrysophanol-1-glucoside, chrysophanol-8-glucoside, emodin-1-glucoside, emodin-8-glucoside, physcion-8-glucoside, physcion-8-gentiobiosiden, aloe-emodin-8-glucoside, aloe-emodin-3-glucoside, and rhein-8-glucoside. Bianthrone glycosides include sennosides A, B, C, D, E, and F. Stilbenes and stilbene glycosides include rhaponticin, rhapontigenin and de-oxyrhaponticin. Radix et Rhizoma Rhei contains a variety of tannins, both hydrolyzable tannins and condensed tannins[4]. Hydrolyzable tannins and its related compounds contain a variety of pentagalloylglucose and 1-O-galloyl-6-O-cinnamoyl-β-D-glucose. Condensed tannins and its related compounds contain catechin, epicatechin and its polymers. In addition, Radix et Rhizoma Rhei also contains a variety of banzylethylketone glycosides.

Production method

Emodin is a plant laxative widely present in plant organs such as roots of Radix et Rhizoma Rhei, bark and root bark of buckthorn and cassia seeds. Emodin can be extracted from roots and rhizomes of Radix et Rhizoma Rhei. It also can be obtained by synthesis, for example, using 2-methyl-anthraquinone, or 3, 5-nitro-phthalic anhydride and m-cresol as the raw material.

Antitumor effect

Pharmacological studies have found that anthraquinone derivatives in Radix et Rhizoma Rhei, rhein, emodin and aloe-emodin showed obvious inhibitory effect on cancers, especially on cancers such as melanoma, P388 leukemia and Ehrlich ascites carcinoma. The polysaccharides contained in Radix et Rhizoma Rhei could markedly inhibit the cells of sarcoma S180. And a concentration of 10 μg/ml emodin could reduce the maximum growth density and the mitotic index of human lung cancer cell line A-549, and apparently decreased the incorporation of tritiated thymidine and the level DNA content. It was also found that the drug could relatively increase the number of cells at the G1 and S stages and decreased the number of aneuploid cells as well as the number of cells at the G2/M phase, with a sinistral displacement of the peak in the DNA histogram. These results suggested that emodin has an obvious inhibitory effect on human lung cancer A-549 cells. The antitumor mechanism of Radix et Rhizoma Rhei is presently considered to be the inhibition of respiration and DNA biosynthesis of cancer cells. It is also believed that rhein and emodin may destroy the cancer cells directly.

Diuretic effect

Both rhein and emodin have evident diuretic effect. The urine volume increased to peak two to four hours after dosing, and in the meanwhile the amounts of Na+ and K+ discharges were also reached to the peak. Aloe-emodin and chrysophanol were less effective in diuretic property as compared with rhein and emodin. The mechanism is contributed to the inhibitory effect of rhein and emodin on renal medullary Na+, K+-ATPase. The Na+ re-absorption in renal tubules is mainly active transport which needs energy from ATP hydrolysis catalyzed by the Na+, K+-ATPase. When the enzyme is inhibited, Na+ re-absorption would decrease because of insufficient energy supply, which leads to water discharge increase along with the increase of Na+ discharge. When distal convoluted tubule Na+ increases, promote Na+-K+ exchange would be promoted, resulting in increase in K+ discharge.

General Description

Orange needles or powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Emodin may be sensitive to prolonged exposure to light. Probably a weak acid due to the phenolic functional groups.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition Emodin emits acrid smoke and irritating fumes.

Fire Hazard

Flash point data for Emodin are not available; however, Emodin is probably combustible.

Biological Activity

Naturally occurring anthraquinone that displays a range of biological activities. Exhibits anti-inflammatory, antitumor and neuroprotective effects.

Biochem/physiol Actions

Cell permeable: yes

Purification Methods

Archin forms orange needles from EtOH, Et2O, *C6H6, toluene or pyridine. It sublimes above 200o at 12mm. [Tutin & Clewer J Chem Soc 99 946 1911, IR: Bloom et al. J Chem Soc 178 1959, UV: Birkinshaw Biochem J 59 495 1955, Raistrick Biochem J 34 159 1940.] 1R,2S-(-)Ephedrine see (-)-ephedrine (1R,2S-2-methylamino-1-phenylpropanol) in “Miscellaneous” in Chapter 6.

Check Digit Verification of cas no

The CAS Registry Mumber 518-82-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,1 and 8 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 518-82:
(5*5)+(4*1)+(3*8)+(2*8)+(1*2)=71
71 % 10 = 1
So 518-82-1 is a valid CAS Registry Number.
InChI:InChI=1/C15H10O5/c1-6-2-8-12(10(17)3-6)15(20)13-9(14(8)19)4-7(16)5-11(13)18/h2-5,16-18H,1H3

518-82-1 Well-known Company Product Price

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  • TCI America

  • (E0500)  Emodin  >96.0%(HPLC)

  • 518-82-1

  • 100mg

  • 570.00CNY

  • Detail
  • TCI America

  • (E0500)  Emodin  >96.0%(HPLC)

  • 518-82-1

  • 1g

  • 2,990.00CNY

  • Detail
  • Sigma

  • (E7881)  Emodin  from Frangula bark, ≥90% (HPLC)

  • 518-82-1

  • E7881-50MG

  • 1,048.32CNY

  • Detail
  • Sigma

  • (E7881)  Emodin  from Frangula bark, ≥90% (HPLC)

  • 518-82-1

  • E7881-250MG

  • 3,641.04CNY

  • Detail

518-82-1SDS

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 emodin

1.2 Other means of identification

Product number -
Other names 6-Methyl-1,3,8-trihydroxyanthraquinone

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:518-82-1 SDS

518-82-1Synthetic route

1,6,8-triacetoxy-3-methyl-9,10-anthraquinone
6030-60-0

1,6,8-triacetoxy-3-methyl-9,10-anthraquinone

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
With sodium hydroxide at 80℃; for 2h;100%
With water; trifluoroacetic acid at 72℃; for 20h;42%
physcion
521-61-9

physcion

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
With boron tribromide In dichloromethane at 0 - 20℃; Inert atmosphere;98%
With hydrogen bromide; acetic acid
With hydrogen bromide
(R)-3,4-dihydro-3,8,9,10-tetrahydroxy-6-methylanthracen-1(2H)-one
1396259-15-6

(R)-3,4-dihydro-3,8,9,10-tetrahydroxy-6-methylanthracen-1(2H)-one

A

Chrysophanol
481-74-3

Chrysophanol

B

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

C

(−)-flavoskyrin
39546-16-2, 115729-00-5

(−)-flavoskyrin

Conditions
ConditionsYield
With oxygen In aq. phosphate buffer; acetonitrile at 10℃; for 10h; pH=6; Solvent;A 10%
B n/a
C 72%
1,3,8-trimethoxy-6-methyl-9,10-anthraquinone
6414-42-2

1,3,8-trimethoxy-6-methyl-9,10-anthraquinone

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
With sulfuric acid at 160℃;
endocrocin
481-70-9

endocrocin

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
at 320℃;
With quinoline; copper oxide-chromium oxide at 170 - 190℃;
2-(2-hydroxy-4-methyl-benzoyl)-3,5-dimethoxy-benzoic acid
54130-71-1

2-(2-hydroxy-4-methyl-benzoyl)-3,5-dimethoxy-benzoic acid

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
With sulfuric acid; sulfur trioxide; boric acid Erhitzen des Reaktionsprodukts mit KBr und H3PO4;
1,3-diamino-8-hydroxy-6-methyl-anthraquinone
861790-72-9

1,3-diamino-8-hydroxy-6-methyl-anthraquinone

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
With sulfuric acid Diazotization.Erhitzen des Reaktionsgemisches auf dem Wasserbad;
With sulfuric acid Diazotization.Erhitzen des Reaktionsgemisches auf dem Wasserbad;
5,7-dihydroxy-1,4-naphthoquinone
4923-54-0

5,7-dihydroxy-1,4-naphthoquinone

3-methyl-1-triethylsilyloxy-1-trimethylsilyloxy-1,3-butadiene
155787-91-0

3-methyl-1-triethylsilyloxy-1-trimethylsilyloxy-1,3-butadiene

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
With hydrogenchloride 1.) toluene, 80-100 deg C, 3 h; 2.) MeOH, rt., 10 h; Yield given. Multistep reaction;
emodin-6,8-di-O-methyl ether
5018-84-8

emodin-6,8-di-O-methyl ether

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
With hydrogen bromide In acetic acid Heating;
With hydrogen bromide In acetic acid for 24h; Heating;6 mg
Multi-step reaction with 2 steps
1: AlCl3
2: HBr
View Scheme
1,2,6,7,8-pentamethoxy-3-methylanthraquinone
81892-82-2

1,2,6,7,8-pentamethoxy-3-methylanthraquinone

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
With chromium(VI) oxide; phosphorus; hydrogen iodide 1.) reflux, 5.5 h; 2.) Ac2O, AcOH, reflux, 2 h; Yield given. Multistep reaction;
euxanmodin A
127506-72-3

euxanmodin A

A

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

B

euxanthone
529-61-3

euxanthone

Conditions
ConditionsYield
With alkaline dithionite
3-((E)-3,7-Dimethyl-octa-2,6-dienyl)-7'-((E)-3,7-dimethyl-octa-2,6-dienyloxy)-2,4,5,4',5'-pentahydroxy-7,2'-dimethyl-9H,9'H-[9,9']bianthracenyl-10,10'-dione

3-((E)-3,7-Dimethyl-octa-2,6-dienyl)-7'-((E)-3,7-dimethyl-octa-2,6-dienyloxy)-2,4,5,4',5'-pentahydroxy-7,2'-dimethyl-9H,9'H-[9,9']bianthracenyl-10,10'-dione

A

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

B

2-geranyl-1,8-dihydroxy-6-methylanthraquinone

2-geranyl-1,8-dihydroxy-6-methylanthraquinone

Conditions
ConditionsYield
With iron(III) chloride In sulfuric acid for 1h; Heating;
vismione D

vismione D

A

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

B

3-geranyloxy-6-methyl-1,8-dihydroxy-anthraquinone
87605-71-8

3-geranyloxy-6-methyl-1,8-dihydroxy-anthraquinone

Conditions
ConditionsYield
In pyridine for 3h; Ambient temperature;
3-geranyloxy-6-methyl-1,8-dihydroxy-anthraquinone
87605-71-8

3-geranyloxy-6-methyl-1,8-dihydroxy-anthraquinone

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
With sulfuric acid In methanol for 5h; Heating;20 mg
Acetic acid 4-hydroxy-5-methoxy-7-methyl-9,10-dioxo-9,10-dihydro-anthracen-2-yl ester

Acetic acid 4-hydroxy-5-methoxy-7-methyl-9,10-dioxo-9,10-dihydro-anthracen-2-yl ester

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
With hydrogen bromide In acetic acid
emodinanthrone
491-60-1

emodinanthrone

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
Product distribution; Mechanism; biotransformation by emodinanthrone oxygenase from Aspergillus terreus: relative activity;
With His-ActVA-ORF5 monooxygenase; His-ActVA-VB monooxygenase; NADH; Flavin mononucleotide; sodium hydroxide; 2,2'-piperazine-1,4-diyl-bis-ethanesulfonic acid; catalase In ethyl methyl ether at 25℃; for 0.166667h; pH=7; Kinetics; Reagent/catalyst; Enzymatic reaction;
emodin anthranol

emodin anthranol

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
With chromium(VI) oxide; acetic acid at 50℃;
emodinol

emodinol

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
With chromium; acetic acid
physcion
521-61-9

physcion

sulfuric acid
7664-93-9

sulfuric acid

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
at 160℃;
sulfuric acid
7664-93-9

sulfuric acid

1,3,8-trimethoxy-6-methyl-9,10-anthraquinone
6414-42-2

1,3,8-trimethoxy-6-methyl-9,10-anthraquinone

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
at 160℃;
emodinanthrone
491-60-1

emodinanthrone

acetic acid
64-19-7

acetic acid

CrO3

CrO3

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

catenarin
476-46-0

catenarin

hydrogen iodide
10034-85-2

hydrogen iodide

acetic acid
64-19-7

acetic acid

red phosphorus

red phosphorus

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
Erwaermen des Reaktionsprodukts mit CrO3 in wss.Essigsaeure;
1,3,8-trimethoxy-6-methyl-9,10-anthraquinone
6414-42-2

1,3,8-trimethoxy-6-methyl-9,10-anthraquinone

AlCl3 (1part )

AlCl3 (1part )

A

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

B

emodinmonomethyl ether

emodinmonomethyl ether

C

emodindimethyl ether (?)

emodindimethyl ether (?)

Conditions
ConditionsYield
at 115℃;
emodin anthrone
491-61-2

emodin anthrone

air oxygen

air oxygen

alkali

alkali

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

3-Methylbutenoic acid
541-47-9

3-Methylbutenoic acid

aqueous HOCl

aqueous HOCl

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 87 percent / 12 h / Heating
2: BuLi/i-Pr2NH / tetrahydrofuran / - 20 deg C, 30 min, then rt., 12 h
3: 2.) 5percent HCl / 1.) toluene, 80-100 deg C, 3 h; 2.) MeOH, rt., 10 h
View Scheme
Trimethylsilyl 3-methyl-2-butenoate
25436-25-3

Trimethylsilyl 3-methyl-2-butenoate

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: BuLi/i-Pr2NH / tetrahydrofuran / - 20 deg C, 30 min, then rt., 12 h
2: 2.) 5percent HCl / 1.) toluene, 80-100 deg C, 3 h; 2.) MeOH, rt., 10 h
View Scheme
vismione D

vismione D

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 3 h / Ambient temperature
2: 20 mg / 2N H2SO4 / methanol / 5 h / Heating
View Scheme
7-methyljuglone
14787-38-3

7-methyljuglone

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: benzene / 24 h / Ambient temperature
2: KOH, sodium nitrosodisulfonate / CH2Cl2; methanol / 2 h / Ambient temperature
3: 92 percent / 0.5 h / 160 °C
4: 35percent aq.HBr / acetic acid / Heating
View Scheme
Multi-step reaction with 3 steps
2: AlCl3
3: HBr
View Scheme
1,4-dihydro-1,3-dimethoxy-8-hydroxy-6-methyl-1,4-ethano-9,10-anthraquinone
139565-30-3

1,4-dihydro-1,3-dimethoxy-8-hydroxy-6-methyl-1,4-ethano-9,10-anthraquinone

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 92 percent / 0.5 h / 160 °C
2: 35percent aq.HBr / acetic acid / Heating
View Scheme
1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

acetic anhydride
108-24-7

acetic anhydride

1,6,8-triacetoxy-3-methyl-9,10-anthraquinone
6030-60-0

1,6,8-triacetoxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
With pyridine at 60 - 70℃; for 4h;98%
With pyridine at 70℃; for 4h;98%
With pyridine at 70℃; for 4h;98%
1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

dimethyl sulfate
77-78-1

dimethyl sulfate

1,3,8-trimethoxy-6-methyl-9,10-anthraquinone
6414-42-2

1,3,8-trimethoxy-6-methyl-9,10-anthraquinone

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium carbonate for 0.333333h; microwave, 600 W (75 deg C);98%
With tetrabutylammomium bromide; potassium carbonate at 75℃; for 0.333333h; microwave irradiation;98%
With potassium carbonate In acetonitrile Inert atmosphere; Reflux;98%
1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

emodinanthrone
491-60-1

emodinanthrone

Conditions
ConditionsYield
With hydrogenchloride; acetic acid; tin(ll) chloride at 120℃; for 24h;98%
With hydrogenchloride; tin(II) chloride dihdyrate; acetic acid for 2h; Reflux; Green chemistry;96%
With hydrogenchloride; acetic acid; tin(ll) chloride In water for 2h; Reflux;95%
1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

emodic acid
478-45-5

emodic acid

Conditions
ConditionsYield
Stage #1: 1,6,8-trihydroxy-3-methyl-9,10-anthraquinone With chromium(VI) oxide In acetic anhydride; acetic acid at 65℃; for 8h;
Stage #2: With sodium carbonate In water
98%
Stage #1: 1,6,8-trihydroxy-3-methyl-9,10-anthraquinone With pyridine at 20℃;
Stage #2: With chromium(VI) oxide; acetic anhydride; acetic acid In water at 45 - 65℃; for 8h;
98%
Multi-step reaction with 3 steps
1: 85 percent / H2SO4 / 0.67 h / 60 °C
2: 84 percent / CrO3 / acetic acid; acetic anhydride / 3.5 h / 70 °C
3: 85 percent / aq. NaOH / 2 h / 80 °C
View Scheme
Multi-step reaction with 3 steps
1: 130 mg / conc. sulfuric acid / 0.5 h / 70 °C
2: 21 mg / chromium(IV) oxide / acetic acid; acetic anhydride / 24 h / Ambient temperature
3: 2 N potassium hydroxide / 0.25 h / 75 °C
View Scheme
Multi-step reaction with 3 steps
1: pyridine / 4 h / 70 °C
2: chromic acid; acetic anhydride; acetic acid; chromium(VI) oxide / 24 h / 70 °C
3: potassium hydroxide / 0.5 h / 70 °C
View Scheme
1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

1-bromoacetone
598-31-2

1-bromoacetone

6-(2-oxopropoxy)-1,8-dihydroxy-3-methylanthra-9,10-quinone

6-(2-oxopropoxy)-1,8-dihydroxy-3-methylanthra-9,10-quinone

Conditions
ConditionsYield
With potassium carbonate In acetone at 45 - 50℃;97%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

3-trifluoromethanesulfonyloxy-1,8-dihydroxy-6-methyl-anthraquinone
401621-24-7

3-trifluoromethanesulfonyloxy-1,8-dihydroxy-6-methyl-anthraquinone

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃; for 4h;95%
1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

ethylenediamine
107-15-3

ethylenediamine

1-((2-aminoethyl)amino)-2,4,5-trihydroxy-7-methylanthracene-9,10-dione

1-((2-aminoethyl)amino)-2,4,5-trihydroxy-7-methylanthracene-9,10-dione

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene at 20℃; for 5h; Inert atmosphere;95%
With [bis(acetoxy)iodo]benzene at 20℃; for 5h;24%
ethyl 3-(chloroformyl)propionate
14794-31-1

ethyl 3-(chloroformyl)propionate

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

1,8-dihydroxy-6-methyl-9,10-anthraquinone-3-oxy ethyl succinate

1,8-dihydroxy-6-methyl-9,10-anthraquinone-3-oxy ethyl succinate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; for 3h;94.7%
1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

4-bromo-3-methyl-1,6,8-trihydroxyanthraquinone
134070-50-1

4-bromo-3-methyl-1,6,8-trihydroxyanthraquinone

Conditions
ConditionsYield
With 1,4-dioxane dibromide In acetic acid at 25℃;94%
1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

7-bromo-1,6,8-trihydroxy-3-methylanthraquinone
18521-77-2

7-bromo-1,6,8-trihydroxy-3-methylanthraquinone

Conditions
ConditionsYield
With 1,4-dioxane dibromide In diethyl ether at 5℃;94%
With bromine In dichloromethane for 3h; Ambient temperature;
1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

methyl iodide
74-88-4

methyl iodide

physcion
521-61-9

physcion

Conditions
ConditionsYield
With potassium carbonate; silver(l) oxide In acetone at 20℃; for 16h;92%
With potassium carbonate In acetone Inert atmosphere; Reflux;77%
With potassium carbonate In acetone for 18h; Reflux;44%
With sodium methylate at 60℃;
1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

hexadecanyl bromide
112-82-3

hexadecanyl bromide

3-hexadecyloxy-1,8-dihydroxy-6-methylanthracene-9,10-dione
1204768-60-4

3-hexadecyloxy-1,8-dihydroxy-6-methylanthracene-9,10-dione

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 20 - 120℃; for 0.25h; Microwave irradiation;90.2%
With potassium carbonate In N,N-dimethyl-formamide at 60 - 70℃; for 4h;
1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

1,3-dibromo-2,4,5-trihydroxy-7-methylanthracene-9,10-dione

1,3-dibromo-2,4,5-trihydroxy-7-methylanthracene-9,10-dione

Conditions
ConditionsYield
With N-Bromosuccinimide In tetrahydrofuran at 0 - 20℃; Reflux; Inert atmosphere;90%
With N-Bromosuccinimide In tetrahydrofuran at 20℃;80%
With N-Bromosuccinimide In tetrahydrofuran at 20℃;
1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

1-dodecylbromide
143-15-7

1-dodecylbromide

3-(dodecyloxy)-1,8-dihydroxy-6-methylanthracene-9,10-dione
1204768-48-8

3-(dodecyloxy)-1,8-dihydroxy-6-methylanthracene-9,10-dione

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 20 - 120℃; for 0.25h; Microwave irradiation;89%
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 4h; Inert atmosphere;78%
With potassium carbonate In N,N-dimethyl-formamide at 60 - 70℃; for 4h;
1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

C15H7Cl8O7P3

C15H7Cl8O7P3

Conditions
ConditionsYield
With phosphorus pentachloride; water In benzene Hydrolysis; phosphorylation;88%
1-bromo-hexane
111-25-1

1-bromo-hexane

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

3-hexyloxy-1,8-dihydroxy-6-methylanthracene-9,10-dione
1204768-25-1

3-hexyloxy-1,8-dihydroxy-6-methylanthracene-9,10-dione

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 20 - 120℃; for 0.25h; Microwave irradiation;87.5%
1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

ethylamine
75-04-7

ethylamine

1-(ethylamino)-2,4,5-trihydroxy-7-methylanthracene-9,10-dione

1-(ethylamino)-2,4,5-trihydroxy-7-methylanthracene-9,10-dione

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene In water at 20℃; for 5h; Inert atmosphere;87%
1-bromo-butane
109-65-9

1-bromo-butane

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

3-butoxy-1,8-dihydroxy-6-methylanthracene-9,10-dione
1204768-17-1

3-butoxy-1,8-dihydroxy-6-methylanthracene-9,10-dione

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 20 - 120℃; for 0.25h; Microwave irradiation;86.7%
1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

3-bromomethyl-1,6,8-trihydroxy-anthraquinone
134070-56-7

3-bromomethyl-1,6,8-trihydroxy-anthraquinone

Conditions
ConditionsYield
With Perbenzoic acid; bromine In 1,4-dioxane for 2h; Heating;86%
1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

1-chloro-2,4,5-trihydroxy-7-methyl-anthracene-9,10-dione

1-chloro-2,4,5-trihydroxy-7-methyl-anthracene-9,10-dione

Conditions
ConditionsYield
With sulfuryl dichloride In dichloromethane; chloroform; acetonitrile at 20℃; for 48h; Inert atmosphere; regioselective reaction;86%
With hydrogenchloride; dihydrogen peroxide; acetic acid at 78℃; for 0.5h;
1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

2,4,5,7-tetrabromo-3-methyl-1,6,8-trihydroxyanthraquinone
134070-53-4

2,4,5,7-tetrabromo-3-methyl-1,6,8-trihydroxyanthraquinone

Conditions
ConditionsYield
With bromine; iodine In tetrachloromethane; ethanol at 170 - 180℃; for 18h;85%
dibutyl hydrogen phosphite
1809-19-4

dibutyl hydrogen phosphite

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

6-dibutoxyphosphinyloxy-1,8-dihydroxy-3-methylanthraquinone

6-dibutoxyphosphinyloxy-1,8-dihydroxy-3-methylanthraquinone

Conditions
ConditionsYield
With triethylamine In tetrachloromethane; isopropyl alcohol for 14h; Ambient temperature;85%
diisopropyl hydrogenphosphonate
1809-20-7

diisopropyl hydrogenphosphonate

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

6-diisopropoxyphosphinyloxy-1,8-dihydroxy-3-methylanthraquinone

6-diisopropoxyphosphinyloxy-1,8-dihydroxy-3-methylanthraquinone

Conditions
ConditionsYield
With triethylamine In tetrachloromethane; isopropyl alcohol for 14h; Ambient temperature;85%
1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

2-iodo-1,3,8-trihydroxy-6-methyl-9,10-dihydroanthracene-9,10-dione

2-iodo-1,3,8-trihydroxy-6-methyl-9,10-dihydroanthracene-9,10-dione

Conditions
ConditionsYield
With iodine; sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃; for 0.5h; w;85%
With iodine; sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃; Reflux; Inert atmosphere;78%
With peracetic acid; phosphoric acid; sodium iodide In ethanol
With iodine; sodium hydrogencarbonate In water
1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

3-bromo-hexan-2-one
29584-99-4

3-bromo-hexan-2-one

6-(1-propyl-2-oxopropoxy)-1,8-dihydroxy-3-methylanthra-9,10-quinone

6-(1-propyl-2-oxopropoxy)-1,8-dihydroxy-3-methylanthra-9,10-quinone

Conditions
ConditionsYield
With potassium carbonate In acetone at 45 - 50℃;85%
1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

(Z)-1-(1,3,8-trihydroxy-9-anthracene-10-on-6-yl)-2-(meso-tetraphenylporphyrin-4-yl)ethene

(Z)-1-(1,3,8-trihydroxy-9-anthracene-10-on-6-yl)-2-(meso-tetraphenylporphyrin-4-yl)ethene

(Z)-1-meso-tetraphenylporphyrin-4-yl-2-(1,8,10,12,13,15-hexahydroxy-dibenzo[oa]perylene-3-yl)ethene

(Z)-1-meso-tetraphenylporphyrin-4-yl-2-(1,8,10,12,13,15-hexahydroxy-dibenzo[oa]perylene-3-yl)ethene

Conditions
ConditionsYield
With potassium tert-butylate In N,N-dimethyl-formamide for 0.5h; Microwave irradiation;85%
1-bromo-octane
111-83-1

1-bromo-octane

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

1,8-dihydroxy-6-methyl-3-octyloxyanthracene-9,10-dione
1204768-32-0

1,8-dihydroxy-6-methyl-3-octyloxyanthracene-9,10-dione

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 20 - 120℃; for 0.25h; Microwave irradiation;84.1%
With potassium carbonate In N,N-dimethyl-formamide at 60 - 70℃; for 4h;
1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

dimethyl amine
124-40-3

dimethyl amine

C25H23NO5
1431545-55-9

C25H23NO5

Conditions
ConditionsYield
In 1,4-dioxane at 65℃; for 24h; Mannich Aminomethylation;83%

518-82-1Relevant articles and documents

ANTHRAQUINONES FROM CASSIA SOPHERA HEARTWOOD

Malhotra, Swadesh,Misra, Krishna

, p. 197 - 200 (1982)

From the heartwood of Cassia sophera two new isomeric anthraquinones, 1,2,7-trihydroxy-6,8-dimethoxy-3-methyl- and 1,2,6-trihydroxy-7,8-dimethoxy-3-methylanthraquinone have been isolated along with 1-octadecanol and quercetin.Key Word Index - Cassia sophera; Leguminosae; heartwood; 1,2,7-trihydroxy-6,8-dimethoxy-3-methylanthraquinone; 1,2,6-trihydroxy-7,8-dimethoxy-3-methylanthraquinone.

PRENYLATED BIANTHRONES AND VISMIONE FROM PSOROSPERMUM FEBRIFUGUM

Botta, B.,Monache, F. Delle,Monache, G. Delle,Bettolo, G. B. Marini,Msonthi, J. D.

, p. 827 - 830 (1985)

Psorospermum febrifugum; Guttiferae; geranyloxyemodin; 2-geranylemodin; vismiones D and F; bianthrones.The roots of Psorospermum febrifugum collected in Malawi contained together with the known vismione D and geranyloxyemodin four new compounds: vismione F and the three bianthrones A1, A3a and A3b.All the isolated compounds contained C- or O-geranyl substituents and showed a close biogenetic relationship.

Enhancement of emodin production by medium optimization and KH2PO4 supplementation in submerged fermentation of marine-derived aspergillus favipes HN4-13

Qiu, Xiaohan,Gong, Lizhi,Xin, Xiujuan,An, Faliang

, (2021)

Emodin is a widely distributed anthraquinone derivative with a variety of biological activities, one that can be efficiently produced by marine-derived fungus Aspergillus favipes HN4-13. However, its relatively low fermentation yield limits further development and pharmaceutical research work. In this study, Plaekett–Burman design and central composite design were adopted to optimize the fermentation conditions of A. favipes HN4-13. Optimal fermentation conditions in a 250-mL Erlenmeyer flask with 50 mL of medium were 59.3 g/L soluble starch, 10 g/L yeast extract paste, 30 g/L seawater salt, 1.04 g/L KH2PO4, 0.05 g/L MgSO4·7H2O, 0.01 g/L FeSO4·7H2O, seed culture 24 h, pH 5, inoculum size 18%, culture temperature 32?C, and shaking at 160 rpm/min for 7 days. The production of emodin could achieve 132.40 ± 3.09 mg/L, with no significant difference from the predicted value (132.47 mg/L). Furthermore, KH2PO4 supplementation strategy was employed to regulate the mycelial morphology, upregulate the transcriptional level of biosynthesis gene cluster, and enhance emodin production (185.56 ± 4.39 mg/L).

Intertwined Biosynthesis of Skyrin and Rugulosin A Underlies the Formation of Cage-Structured Bisanthraquinones

Bai, Wei,Ding, Chun Xia,Han, Yun Bin,Liang, Jie,Tan, Ren Xiang,Wu, Shao-Hua

supporting information, p. 14218 - 14226 (2021/09/13)

Skyrin and rugulosin A are bioactive bisanthraquinones found in many fungi, with the former suggested as a precursor of hypericin (a diversely bioactive phytochemical) and the latter characterized by its distinct cage-like structure. However, their biosynthetic pathways remain mysterious, although they have been characterized for over six decades. Here, we present the rug gene cluster that governs simultaneously the biosynthesis of skyrin and rugulosin A in Talaromyces sp. YE3016, a fungal endophyte residing in Aconitum carmichaeli. A combination of genome sequencing, gene inactivation, heterologous expression, and biotransformation tests allowed the identification of the gene function, biosynthetic precursor, and enzymatic sets involved in their molecular architecture constructions. In particular, skyrin was demonstrated to form from the 5,5′-dimerization of emodin radicals catalyzed by RugG, a cytochrome P450 monooxygenase evidenced to be potentially applicable for the (chemo)enzymatic synthesis of dimeric polyphenols. The fungal aldo-keto reductase RugH was shown to be capable of hijacking the closest skyrin precursor (CSP) immediately after the emodin radical coupling, catalyzing the ketone reduction of CSP to inactivate its tautomerization into skyrin and thus allowing for the spontaneous intramolecular Michael addition to cyclize the ketone-reduced form of CSP into rugulosin A, a representative of diverse cage-structured bisanthraquinones. Collectively, the work updates our understanding of bisanthraquinone biosynthesis and paves the way for synthetic biology accesses to skyrin, rugulosin A, and their siblings.

Synthesis and antibacterial activity of emodin and its derivatives against methicillin-resistant Staphylococcus aureus

Chalothorn, Thidarat,Rukachaisirikul, Vatcharin,Phongpaichit, Souwalak,Pannara, Sakawrat,Tansakul, Chittreeya

supporting information, (2019/08/08)

Synthesis of the antibacterial emodin was improved using Friedel-Crafts acylation as a key step leading to 37% overall yield. In addition, 21 analogues were synthesized by structural modification of the hydroxyl and methyl groups, as well as the aromatic ring of emodin. Antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) and cytotoxicity against noncancerous Vero cells were evaluated. A structure-activity relationship (SAR) study indicated that the hydroxyl groups and the methyl group in the emodin skeleton were crucial for anti-MRSA activity. Furthermore, the presence of an iodine atom or ethylamino group on the aromatic ring enhanced the anti-MRSA activity with higher selectivity indices, while derivatives containing bromine, chlorine atoms or quaternary ammonium salt were as active as emodin. The quaternary ammonium group on the aromatic ring also led to non-cytotoxicity against Vero cells.

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