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2D Structure
Also known as: 84604-20-6, Milkthistleextract, 65666-07-1, A835184, (2s)-3,5,7-trihydroxy-2-[(2s,3r)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one, (2s)-3,5,7-trihydroxy-2-[(2s,3r)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2h-1-benzopyran-4-one
Molecular Formula
C25H22O10
Molecular Weight
482.4  g/mol
InChI Key
SEBFKMXJBCUCAI-VGHNRKBZSA-N

1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S)-3,5,7-trihydroxy-2-[(2S,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one
2.1.2 InChI
InChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-16-5-3-12(7-18(16)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3/t20-,23?,24+,25-/m0/s1
2.1.3 InChI Key
SEBFKMXJBCUCAI-VGHNRKBZSA-N
2.1.4 Canonical SMILES
COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=C(C=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O
2.1.5 Isomeric SMILES
COC1=C(C=CC(=C1)[C@@H]2[C@@H](OC3=C(O2)C=C(C=C3)[C@H]4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O
2.2 Synonyms
2.2.1 Depositor-Supplied Synonyms

1. 84604-20-6

2. Milkthistleextract

3. 65666-07-1

4. A835184

5. (2s)-3,5,7-trihydroxy-2-[(2s,3r)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one

6. (2s)-3,5,7-trihydroxy-2-[(2s,3r)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2h-1-benzopyran-4-one

2.3 Create Date
2009-08-20
3 Chemical and Physical Properties
Molecular Weight 482.4 g/mol
Molecular Formula C25H22O10
XLogP32.4
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count10
Rotatable Bond Count4
Exact Mass482.12129689 g/mol
Monoisotopic Mass482.12129689 g/mol
Topological Polar Surface Area155 Ų
Heavy Atom Count35
Formal Charge0
Complexity750
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

EXPL THER The 2008 Hepatitis C Antiviral Long-Term Treatment Against Cirrhosis (HALT-C) study, sponsored by the National Institutes of Health (NIH), found that hepatitis C patients who used silymarin had fewer and milder symptoms of liver disease and somewhat better quality of life but no change in virus activity or liver inflammation.

NIH National Center forComplementary and Alternative Medicine; Milk Thistle; Available from, as of November 4, 2013: https://nccam.nih.gov/health/milkthistle/ataglance.htm


EXPL THER A 2012 clinical trial, cofunded by NCCAM and the National Institute of Diabetes and Digestive and Kidney Diseases, showed that two higher-than-usual doses of silymarin were no better than placebo for chronic hepatitis C in people who had not responded to standard antiviral treatment.

NIH National Center forComplementary and Alternative Medicine; Milk Thistle; Available from, as of November 4, 2013: https://nccam.nih.gov/health/milkthistle/ataglance.htm


EXPL THER ...laboratory studies suggested that milk thistle may benefit the liver by protecting and promoting the growth of liver cells, fighting oxidation (a chemical process that can damage cells), and inhibiting inflammation. However, results from small clinical trials of milk thistle for liver diseases have been mixed, and two rigorously designed studies found no benefit.

NIH National Center forComplementary and Alternative Medicine; Milk Thistle; Available from, as of November 4, 2013: https://nccam.nih.gov/health/milkthistle/ataglance.htm


EXPL THER Silymarin has been used in pregnant women who have a bile blockage in the liver, with no toxic effects to the patient or fetus. Silymarin have also been given to children intravenously for mushroom poisoning.

National Cancer Institute; Milk Thistle PDQ; Available from, as of November 2013: https://www.cancer.gov/cancertopics/pdq/cam/milkthistle/Patient/Page2#Section_10


For more Therapeutic Uses (Complete) data for Milk Thistle Extract (16 total), please visit the HSDB record page.


4.2 Drug Warning

Milk thistle may lower blood sugar levels. People with diabetes or hypoglycemia, or people taking drugs or supplements that affect blood sugar levels, should use caution.

NIH National Center forComplementary and Alternative Medicine; Milk Thistle; Available from, as of November 4, 2013: https://nccam.nih.gov/health/milkthistle/ataglance.htm


Milk thistle can produce allergic reactions, which tend to be more common among people who are allergic to plants in the same family (for example, ragweed, chrysanthemum, marigold, and daisy).

NIH National Center forComplementary and Alternative Medicine; Milk Thistle; Available from, as of November 4, 2013: https://nccam.nih.gov/health/milkthistle/ataglance.htm


In clinical trials, milk thistle appears to be well tolerated in recommended doses. Occasionally, people report various gastrointestinal side effects.

NIH National Center forComplementary and Alternative Medicine; Milk Thistle; Available from, as of November 4, 2013: https://nccam.nih.gov/health/milkthistle/ataglance.htm