10351-88-9

Basic information

• Product Name: PHYLLANTHIN
• Synonyms: PHYLLANTHIN;PHOSPHO-L-SERINE, O-(RG);1,1'-[(2S,3S)-2,3-Bis(methoxymethyl)-1,4-butanediyl]bis[3,4-dimethoxybenzene];NSC 619043;Phyllanthin (15 mg);3,3',4,4',9,9'-HexaMethoxylignan;Tetra-O-Methylsecoisolariciresinol;(2S,3S)-(+)-1,4-Dimethoxy-2,3-diveratrylbutane
• CAS NO: 10351-88-9
• Molecular Formula: C₂₄H₃₄O₆
• Molecular Weight: 247.29
• Mol File: 10351-88-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: 96℃
• Boiling Point: 530.6°Cat760mmHg
• Flash Point: 207.3°C
• Appearance: /
• Density: 1.069
• BRN: 2066503
• CAS DataBase Reference: PHYLLANTHIN(CAS DataBase Reference)
• NIST Chemistry Reference: PHYLLANTHIN(10351-88-9)
• EPA Substance Registry System: PHYLLANTHIN(10351-88-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 10351-88-9(Hazardous Substances Data)

Usage

Uses

Phyllanthin is a chemical extract from the Phyllanthus niruri plant and displays pharmacological effects as an anti-diabetic action, anti-arthritic, and inhibitor of P-gp.

Synthetic route

Dg-threo-2,3-bis-(3,4-dimethoxy-benzyl)-butanediol-(1,4) (10352-25-7) + methyl iodide (74-88-4) → (+)-phyllanthin (10351-88-9)

Conditions	Yield
With silver(l) oxide In N,N-dimethyl-formamide

C22H26O6 + methyl iodide (74-88-4) → (+)-phyllanthin (10351-88-9)

Conditions	Yield
(i) Li, EtOH, liq. NH3, (ii) NaH, benzene, (iii) /BRN= 969135/; Multistep reaction;

methyl iodide (74-88-4) + (-)-tetrahydroeudesmyne → (+)-phyllanthin (10351-88-9)

Conditions	Yield
With sodium hydride

Dg-threo-2.3-bis-(3.4-dimethoxy-benzyl)-succinic acid (15813-34-0, 15905-29-0, 93609-04-2, 126965-32-0) → (+)-phyllanthin (10351-88-9)

Conditions	Yield
Multi-step reaction with 3 steps 2: LiAlH4 / tetrahydrofuran 3: Ag2O / dimethylformamide View Scheme

D,L-2,3-bis(3,4-dimethoxybenzyl)succinic acid (15813-34-0, 15905-29-0, 93609-04-2, 126965-32-0) → (+)-phyllanthin (10351-88-9)

Conditions	Yield
Multi-step reaction with 4 steps 3: LiAlH4 / tetrahydrofuran 4: Ag2O / dimethylformamide View Scheme

(+)-2,3-Diveratryl-bernsteinsaeure-dimethylester → (+)-phyllanthin (10351-88-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4 / tetrahydrofuran 2: Ag2O / dimethylformamide View Scheme

(+)-phyllanthin (10351-88-9) → 4-(3,4-Dimethoxy-phenyl)-6,7-dimethoxy-3-methoxymethyl-naphthalene-2-carbaldehyde (79606-73-8)

Conditions	Yield
With acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone at 50℃; for 0.666667h; sonication;	92%

(+)-phyllanthin (10351-88-9) → 3,4,3',4'-tetramethoxy-9,9'-epoxylignan (10352-26-8)

Conditions	Yield
With trifluoroacetic anhydride; trichlorophosphate In benzene for 6h; Heating;	45%

(+)-phyllanthin (10351-88-9) → (S:S)-1,4-dimethoxy-2,3-bis-(6-bromo-3,4-dimethoxy-benzyl)-butane (138737-28-7)

Conditions	Yield
With chloroform; bromine

(+)-phyllanthin (10351-88-9) → Dinitrophyllanthin

Conditions	Yield
With nitric acid In acetic acid

chloroform (67-66-3) + (+)-phyllanthin (10351-88-9) + bromine (7726-95-6) → (S:S)-1,4-dimethoxy-2,3-bis-(6-bromo-3,4-dimethoxy-benzyl)-butane (138737-28-7)

(+)-phyllanthin (10351-88-9) → 1-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-2,3-dimethyl-naphthalene (5811-91-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 92 percent / H2; acetic acid / Pd/C / ethyl acetate / 18 h / 20 °C View Scheme

(+)-phyllanthin (10351-88-9) → dehydrodimethylconidendrin (6258-38-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 85 percent / NaClO2; 2-methylbutene; NaH2PO4 / H2O; 2-methyl-propan-2-ol / 20 °C 3: 98 percent / trifluoroacetic acid / acetonitrile / 24 h / 20 °C View Scheme

(+)-phyllanthin (10351-88-9) → 4,5,3',4'-tetrahydroxy-2,7'-cycloligna-7,7'-diene-9,9'-lactone (741292-75-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 85 percent / NaClO2; 2-methylbutene; NaH2PO4 / H2O; 2-methyl-propan-2-ol / 20 °C 3: 98 percent / trifluoroacetic acid / acetonitrile / 24 h / 20 °C 4: 79 percent / pyridinium hydrochloride / 0.5 h / 190 °C View Scheme

(+)-phyllanthin (10351-88-9) → 5-(3,4-dihydroxy-phenyl)-6,7-dimethyl-naphthalene-2,3-diol (741292-76-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 92 percent / H2; acetic acid / Pd/C / ethyl acetate / 18 h / 20 °C 3: 57 percent / pyridinium hydrochloride / 0.5 h / 190 °C View Scheme

(+)-phyllanthin (10351-88-9) → 3-bromomethyl-4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-naphthalene-2-carbaldehyde (741292-78-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 89 percent / HBr / CH2Cl2 / 3 h / 20 °C View Scheme

(+)-phyllanthin (10351-88-9) → 4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-2-methyl-2,3-dihydro-1H-benzo[f]isoindole

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 89 percent / HBr / CH2Cl2 / 3 h / 20 °C 3: 51 percent / CH2Cl2 / 3 h 4: 74 percent / sodium borohydride / methanol / 0.5 h / 20 °C View Scheme

(+)-phyllanthin (10351-88-9) → [4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-3-methoxymethyl-naphthalen-2-yl]-methanol

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 75 percent / NaBH4 / CH2Cl2; methanol / 10 h / 20 °C View Scheme

(+)-phyllanthin (10351-88-9) → 4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-3-methoxymethyl-naphthalene-2-carboxylic acid (741292-74-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 85 percent / NaClO2; 2-methylbutene; NaH2PO4 / H2O; 2-methyl-propan-2-ol / 20 °C View Scheme

(+)-phyllanthin (10351-88-9) → 4-(3,4-dimethoxy-phenyl)-2-isopropyl-6,7-dimethoxy-2,3-dihydro-1H-benzo[f]isoindole

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 89 percent / HBr / CH2Cl2 / 3 h / 20 °C 3: 46 percent / CH2Cl2 4: 74 percent / sodium borohydride / methanol / 20 °C View Scheme

(+)-phyllanthin (10351-88-9) → [4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-3-methoxymethyl-naphthalen-2-ylmethyl]-methyl-amine

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2.1: methanol / 0.17 h 2.2: 99 percent / NaBH4 / methanol / 0.5 h / 20 °C View Scheme

(+)-phyllanthin (10351-88-9) → 6',9'-dibromo-4,5,3',4'-tetramethoxy-9-oxo-2,7'-cycloligna-7,7'-diene

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 89 percent / HBr / CH2Cl2 / 3 h / 20 °C 3: 10 mg / Br2 View Scheme

(+)-phyllanthin (10351-88-9) → 8-bromo-3-bromomethyl-4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-naphthalene-2-carbaldehyde (741292-79-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 89 percent / HBr / CH2Cl2 / 3 h / 20 °C 3: 61 mg / Br2 View Scheme

(+)-phyllanthin (10351-88-9) → 4-(3,4-dimethoxy-phenyl)-2-isobutyl-6,7-dimethoxy-2,3-dihydro-1H-benzo[f]isoindole

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 89 percent / HBr / CH2Cl2 / 3 h / 20 °C 3: 58 percent / CH2Cl2 4: 72 percent / sodium borohydride / methanol / 20 °C View Scheme

(+)-phyllanthin (10351-88-9) → [4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-3-methoxymethyl-naphthalen-2-ylmethyl]-isopropyl-amine

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2.1: methanol 2.2: 98 percent / NaBH4 / methanol / 20 °C View Scheme

(+)-phyllanthin (10351-88-9) → 5-bromo-1-(3',4'-dihydroxyphenyl)-6,7-dimethoxy-N-methyl-2'',5''H-pyrrolo[4,3-b]naphthalene

Conditions	Yield
Multi-step reaction with 5 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 89 percent / HBr / CH2Cl2 / 3 h / 20 °C 3: 61 mg / Br2 4: 65 percent / CH2Cl2 5: 75 percent / sodium borohydride / methanol / 20 °C View Scheme

(+)-phyllanthin (10351-88-9) → 4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-2-propyl-2,3-dihydro-1H-benzo[f]isoindole

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 89 percent / HBr / CH2Cl2 / 3 h / 20 °C 3: 41 percent / CH2Cl2 4: 66 percent / sodium borohydride / methanol / 20 °C View Scheme

(+)-phyllanthin (10351-88-9) → [4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-3-methoxymethyl-naphthalen-2-ylmethyl]-propyl-amine

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2.1: methanol 2.2: 98 percent / NaBH4 / methanol / 20 °C View Scheme

(+)-phyllanthin (10351-88-9) → [4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-3-methoxymethyl-naphthalen-2-ylmethyl]-isobutyl-amine

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2.1: methanol 2.2: 98 percent / NaBH4 / methanol / 20 °C View Scheme

(+)-phyllanthin (10351-88-9) → 9-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-2-methyl-3-methylamino-1H-benzo[f]isoindolium; bromide

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 89 percent / HBr / CH2Cl2 / 3 h / 20 °C 3: 51 percent / CH2Cl2 / 3 h View Scheme

(+)-phyllanthin (10351-88-9) → 5-bromo-9-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-2-methyl-3-methylamino-1H-benzo[f]isoindolium; bromide

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 89 percent / HBr / CH2Cl2 / 3 h / 20 °C 3: 61 mg / Br2 4: 65 percent / CH2Cl2 View Scheme

(+)-phyllanthin (10351-88-9) → 9-(3,4-dimethoxy-phenyl)-2-isopropyl-3-isopropylamino-6,7-dimethoxy-1H-benzo[f]isoindolium; bromide

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 89 percent / HBr / CH2Cl2 / 3 h / 20 °C 3: 46 percent / CH2Cl2 View Scheme

Upstream product

• 10352-25-7 D_g-threo-2,3-bis-(3,4-dimethoxy-benzyl)-butanediol-(1,4) 
• 74-88-4 methyl iodide 
• 58311-18-5 (2R,3R)-2,3-bis[(3,4-dimethoxyphenyl)methyl]butane-1,4-diol 
• 138737-28-7 bromophyllanthin 
• 15813-34-0 D,L-2,3-bis(3,4-dimethoxybenzyl)succinic acid 
• 15813-34-0 (1R,2R)-1,2-bis[(3,4-dimethoxyphenyl)methyl]ethane-1,2-dicarboxylic acid 
• 15813-34-0 D_g-threo-2.3-bis-(3.4-dimethoxy-benzyl)-succinic acid 

Downstream Products

• 138737-28-7 (S:S)-1,4-dimethoxy-2,3-bis-(6-bromo-3,4-dimethoxy-benzyl)-butane 
• 79606-73-8 4-(3,4-Dimethoxy-phenyl)-6,7-dimethoxy-3-methoxymethyl-naphthalene-2-carbaldehyde 
• 10352-26-8 3,4,3',4'-tetramethoxy-9,9'-epoxylignan 
• 138737-31-2 (3R,4R)-3,4-Bis-(2-bromo-4,5-dimethoxy-benzyl)-tetrahydro-furan 
• 741292-79-5 8-bromo-3-bromomethyl-4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-naphthalene-2-carbaldehyde 
• 741292-74-0 4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-3-methoxymethyl-naphthalene-2-carboxylic acid 
• 741292-78-4 3-bromomethyl-4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-naphthalene-2-carbaldehyde 
• 741292-75-1 4,5,3',4'-tetrahydroxy-2,7'-cycloligna-7,7'-diene-9,9'-lactone 

Related news

Investigation of anticancer potential of hypoPHYLLANTHIN (cas 10351-88-9) and PHYLLANTHIN (cas 10351-88-9) against breast cancer by in vitro and in vivo methods08/06/2019

ObjectiveTo investigate the in vitro and in vivo anticancer activities of hypophyllanthin and phyllanthin isolated from Phyllanthus amarus Schum & Thonn against breast cancer.detailed

Immobilization mediated enhancement of PHYLLANTHIN (cas 10351-88-9) and hypoPHYLLANTHIN (cas 10351-88-9) from Phyllanthus amarus08/05/2019

ABSTRACTPhyllanthus amarus plant is used in the traditional system of medicine as a hepatoprotective drug for which the major lignans phyllanthin and hypophyllanthin are responsible. So far, no significant work has been done on the culture of this plant. Realizing the hepatoprotective potential,...detailed

Determination of PHYLLANTHIN (cas 10351-88-9) and Gallic Acid In Herbal Hepatoprotective Formulation By TLC-Densitometry Analysis08/04/2019

Introduction: Phyllanthus niruri, Andrographis paniculata and Embilica officinalis are most important and high value medicinal plant known for its hepatoprotective activity. Several analytical methods including HPTLC and HPLC are reported for respective phytoconstituents. However, there is no si...detailed

Endothelium-independent effects of PHYLLANTHIN (cas 10351-88-9) and hypoPHYLLANTHIN (cas 10351-88-9) on vascular tension08/03/2019

The purpose of this study was to investigate the modulating effects of phyllanthin and hypophyllanthin on vascular tension, using in the in vitro model of isolated rat aorta. Our results indicated that both phyllanthin and hypophyllanthin significantly relaxed the sustained contraction induced b...detailed

Ameliorative effects of PHYLLANTHIN (cas 10351-88-9) on carbon tetrachloride-induced hepatic oxidative damage in mice08/01/2019

ObjectiveTo evaluate the liver protecting efficacy of phyllanthin, a lignin, isolated from the leaves of Phyllanthus amarus using mice model.detailed

PHYLLANTHIN (cas 10351-88-9) from Phyllanthus amarus inhibits cellular and humoral immune responses in Balb/C mice07/31/2019

BackgroundPhyllanthin found in many Phyllanthus species has various biochemical and pharmacological properties especially on its hepatoprotective effects. However, its effect on the immune system has not been well documented.detailed

HPLC fingerprint and simultaneous quantitative analysis of PHYLLANTHIN (cas 10351-88-9) and hypoPHYLLANTHIN (cas 10351-88-9) for identification and authentication of Phyllanthus niruri from related species07/30/2019

A precise and accurate method for the identification and authentication of Phyllanthus niruri L. from P. debilis Klein ex Willd. and P. urinaria L., Phyllanthaceae, was developed using high-performance liquid chromatography. Chromatographic fingerprint analysis was combined with simultaneous qua...detailed

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