Sulforaphane

Synopsis, Chemistry

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Also known as: 4478-93-7, Dl-sulforaphane, 1-isothiocyanato-4-(methylsulfinyl)butane, Sulforafan, D,l-sulforaphane, 1-isothiocyanato-4-methylsulfinylbutane

Molecular Formula

C₆H₁₁NOS₂

Molecular Weight

177.3 g/mol

InChI Key

SUVMJBTUFCVSAD-UHFFFAOYSA-N

FDA UNII

41684WL1GL

Sulforaphane is a naturally-occurring phytochemical belonging to the class of isothiocyanates. As the aglycone metabolite of glucosinolate glucoraphanin (sulforaphane glucosinolate), sulforaphane acts as an antioxidant and potent stimulator of endogenous detoxifying enzymes. This agent displays anticarcinogenic properties due to its ability to induce phase II detoxification enzymes, such as glutathione S-transferase and quinone reductase, thereby providing protection against certain carcinogens and toxic, reactive oxygen species. Broccoli sprouts contain large amounts of sulforaphane, which is also found in other cruciferous vegetables including cabbage and kale. (NCI04)

1 2D Structure

Sulforaphane

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-isothiocyanato-4-methylsulfinylbutane

2.1.2 InChI

InChI=1S/C6H11NOS2/c1-10(8)5-3-2-4-7-6-9/h2-5H2,1H3

2.1.3 InChI Key

SUVMJBTUFCVSAD-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CS(=O)CCCCN=C=S

2.2 Other Identifiers

2.2.1 UNII

41684WL1GL

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (+-)-sulforaphane

2. (r)-sulforaphane

3. (s)-sulforaphane

4. 1-isothiocyanato-4-methylsulphinylbutane

5. 4-methylsulfoxybutylisothiocyanate

6. Sulforafan

7. Sulforaphane, (r)-

8. Sulphoraphane

2.3.2 Depositor-Supplied Synonyms

1. 4478-93-7

2. Dl-sulforaphane

3. 1-isothiocyanato-4-(methylsulfinyl)butane

4. Sulforafan

5. D,l-sulforaphane

6. 1-isothiocyanato-4-methylsulfinylbutane

7. Butane, 1-isothiocyanato-4-(methylsulfinyl)-

8. 1-isothiocyanato-4-(methylsulfinyl)-butane

9. (+/-)-sulforaphane

10. Chebi:47807

11. 41684wl1gl

12. 4-(methylsulfinyl)butyl Isothiocyanate

13. Nsc-749790

14. Sulforaphane, (r)-

15. (s)-1-isothiocyanato-4-(methylsulfinyl)butane

16. R,s-sulforaphane

17. Sulphoraphane

18. Sulforaphane (unspecified)

19. Sfn

20. Sulforaphane Extract

21. Ccris 7221

22. Broccoli Sprout Extracts

23. Butane, 1-isothiocyanato-4-[(s)-methylsulfinyl]-

24. Sulforathane

25. Unii-41684wl1gl

26. S)-sulforaphane

27. D,l-sulforaphane-[d8]

28. Butane,1-isothiocyanato-4-(methylsulfinyl)-

29. Chembl48802

30. Schembl105202

31. Gtpl6569

32. Dtxsid8036732

33. Sulforaphane, (+/-)-

34. Hms3746m17

35. Bcp31547

36. 4-methylsulfinyl Butyl Isothiocyanate

37. Bdbm50073654

38. Mfcd00198068

39. Nsc749790

40. S5771

41. 4-isothiocyanatobutyl Methyl Sulfoxide

42. Akos006282481

43. Cs-7809

44. Nsc 749790

45. 4-(methylsulfinyl)-butyl Isothiocyanate

46. Sulforaphane (+/-)-form [mi]

47. 1-isothiocyanato-4-methylsulfinyl-butane

48. Ac-34421

49. Hy-13755

50. 1-isothiocyanato-4-(methylsulfinyl)butane #

51. Ft-0674748

52. Ft-0674749

53. Ft-0674750

54. Ft-0674751

55. U0142

56. F17072

57. 478s937

58. A912495

59. Q424489

60. Dl-sulforaphane, >=90% (hplc), Synthetic, Liquid

61. Q-100160

62. Brd-a58955223-001-02-0

63. Isothiocyanic Acid, 4-(methylsulfinyl)butyl Ester

64. (r)-sulforaphane;(-)-sulforaphane;4-methylsulfinylbutyl Isothiocyanate

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₆H₁₁NOS₂
Molecular Weight	177.3 g/mol
XLogP3	1.4
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	5
Exact Mass	177.02820632 g/mol
Monoisotopic Mass	177.02820632 g/mol
Topological Polar Surface Area	80.7 Å²
Heavy Atom Count	10
Formal Charge	0
Complexity	152
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Anticarcinogenic Agents

Agents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved. (See all compounds classified as Anticarcinogenic Agents.)