Sulforaphane
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MedKoo CAT#: 202713

CAS#: 4478-93-7 (racemic)

Description: Sulforaphane, also known as BroccoPhane; Sulphoraphane; Detoxophane, 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.


Chemical Structure

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Sulforaphane
CAS# 4478-93-7 (racemic)

Theoretical Analysis

MedKoo Cat#: 202713
Name: Sulforaphane
CAS#: 4478-93-7 (racemic)
Chemical Formula: C6H11NOS2
Exact Mass: 177.02821
Molecular Weight: 177.29
Elemental Analysis: C, 40.65; H, 6.25; N, 7.90; O, 9.02; S, 36.17

Price and Availability

Size Price Availability Quantity
100.0mg USD 150.0 Ready to ship
250.0mg USD 250.0 Ready to ship
500.0mg USD 550.0 Ready to ship
1.0g USD 950.0 Ready to ship
2.0g USD 1650.0 Ready to ship
5.0g USD 3250.0 Ready to ship
10.0g USD 5850.0 Ready to ship
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Related CAS #: 142825-10-3 (R-isomer)   155320-20-0 (S-isomer)   4478-93-7 (racemic)    

Synonym: Broccoli sprout extracts; 4-methyl-sulfinybutyl isothiocyanatel; Sulforafan; Sulforaphane; BroccoPhane; Detoxophane; Sulphoraphane;

IUPAC/Chemical Name: 1-isothiocyanato-4-(methylsulfinyl)butane

InChi Key: SUVMJBTUFCVSAD-UHFFFAOYSA-N

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

SMILES Code: O=S(CCCCN=C=S)C

Appearance: Colorless to yellow-brown oil

Purity: >95% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Biological target: Sulforaphane is an inducer of Nrf2 and is also an inhibitor of histone deacetylase (HDAC) and NF-κB.
In vitro activity: H9c2 rat myoblasts were pre-treated with sulforaphane and its effects on cardiotoxicity were then examined. The results revealed that the pre-treatment of H9c2 rat myoblasts with sulforaphane decreased the apoptotic cell number (as shown by trypan blue exclusion assay) and the expression of pro-apoptotic proteins (Bax, caspase-3 and cytochrome c; as shown by western blot analysis and immunostaining), as well as the doxorubicin-induced increase in mitochondrial membrane potential (measured by JC-1 assay). Furthermore, sulforaphane increased the mRNA and protein expression of heme oxygenase-1 (HO-1, measured by RT-qPCR), which consequently reduced the levels of reactive oxygen species (ROS, measured using MitoSOX Red reagent) in the mitochondria which were induced by doxorubicin. The cardioprotective effects of sulforaphane were found to be mediated by the activation of the Kelch-like ECH-associated protein 1 (Keap1)/NF-E2-related factor-2 (Nrf2)/antioxidant-responsive element (ARE) pathway, which in turn mediates the induction of HO-1. Taken together, the findings of this study demonstrate that sulforaphane prevents doxorubicin-induced oxidative stress and cell death in H9c2 cells through the induction of HO-1 expression. Reference: Int J Mol Med. 2015 Jul;36(1):53-64. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/25936432/
In vivo activity: N-butyl-N-(4-hydroxybutyl)-nitrosamine is used to induce bladder cancer in male C57BL/6 mice, with or without sulforaphane (SFN) for 23 weeks. SFN ameliorates the histological changes characteristic of bladder cancer, resulting in fewer submucosal capillaries. SFN normalizes gut microbiota dysbiosis in mice with BBN-induced bladder cancer with a significant increase in Bacteroides fragilis and Clostridium cluster I. SFN also increases butyric acid levels in the mouse colon, and repairs the injury to the mucosal epithelium of the colon and cecum through the upregulation of the expression of tight junction proteins and GLP2. SFN greatly decreases the release of cytokines (IL-6) and secretory immunoglobulin A in the mice with bladder cancer. Reference: Mol Nutr Food Res. 2018 Dec;62(24):e1800427. https://doi.org/10.1002/mnfr.201800427

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 62.5 352.53

Preparing Stock Solutions

The following data is based on the product molecular weight 177.29 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
In vitro protocol: 1. Li B, Kim DS, Yadav RK, Kim HR, Chae HJ. Sulforaphane prevents doxorubicin-induced oxidative stress and cell death in rat H9c2 cells. Int J Mol Med. 2015 Jul;36(1):53-64. doi: 10.3892/ijmm.2015.2199. Epub 2015 Apr 28. PMID: 25936432; PMCID: PMC4494600.
In vivo protocol: 1. He C, Huang L, Lei P, Liu X, Li B, Shan Y. Sulforaphane Normalizes Intestinal Flora and Enhances Gut Barrier in Mice with BBN-Induced Bladder Cancer. Mol Nutr Food Res. 2018 Dec;62(24):e1800427. doi: 10.1002/mnfr.201800427. Epub 2018 Nov 22. PMID: 30302904.

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1: Sharma R, Sharma A, Chaudhary P, Sahu M, Jaiswal S, Awasthi S, Awasthi YC. Role of 4-hydroxynonenal in chemopreventive activities of sulforaphane. Free Radic Biol Med. 2012 Jun 1-15;52(11-12):2177-85. doi: 10.1016/j.freeradbiomed.2012.04.012. Epub 2012 Apr 23. Review. PubMed PMID: 22579574; PubMed Central PMCID: PMC3377772.

2: Liang H, Yuan Q. Natural sulforaphane as a functional chemopreventive agent: including a review of isolation, purification and analysis methods. Crit Rev Biotechnol. 2012 Sep;32(3):218-34. doi: 10.3109/07388551.2011.604838. Epub 2011 Sep 27. Review. PubMed PMID: 21942647.

3: Keum YS. Regulation of the Keap1/Nrf2 system by chemopreventive sulforaphane: implications of posttranslational modifications. Ann N Y Acad Sci. 2011 Jul;1229:184-9. doi: 10.1111/j.1749-6632.2011.06092.x. Review. PubMed PMID: 21793854.

4: Kaminski BM, Steinhilber D, Stein JM, Ulrich S. Phytochemicals resveratrol and sulforaphane as potential agents for enhancing the anti-tumor activities of conventional cancer therapies. Curr Pharm Biotechnol. 2012 Jan;13(1):137-46. Review. PubMed PMID: 21466425.

5: Tomczyk J, Olejnik A. [Sulforaphane--a possible agent in prevention and therapy of cancer]. Postepy Hig Med Dosw (Online). 2010 Nov 29;64:590-603. Review. Polish. PubMed PMID: 21160094.

6: Guerrero-Beltrán CE, Calderón-Oliver M, Pedraza-Chaverri J, Chirino YI. Protective effect of sulforaphane against oxidative stress: recent advances. Exp Toxicol Pathol. 2012 Jul;64(5):503-8. doi: 10.1016/j.etp.2010.11.005. Epub 2010 Dec 3. Review. PubMed PMID: 21129940.

7: Cheung KL, Kong AN. Molecular targets of dietary phenethyl isothiocyanate and sulforaphane for cancer chemoprevention. AAPS J. 2010 Mar;12(1):87-97. doi: 10.1208/s12248-009-9162-8. Epub 2009 Dec 15. Review. PubMed PMID: 20013083; PubMed Central PMCID: PMC2811646.

8: Nian H, Delage B, Ho E, Dashwood RH. Modulation of histone deacetylase activity by dietary isothiocyanates and allyl sulfides: studies with sulforaphane and garlic organosulfur compounds. Environ Mol Mutagen. 2009 Apr;50(3):213-21. doi: 10.1002/em.20454. Review. PubMed PMID: 19197985; PubMed Central PMCID: PMC2701665.

9: Fimognari C, Lenzi M, Hrelia P. Interaction of the isothiocyanate sulforaphane with drug disposition and metabolism: pharmacological and toxicological implications. Curr Drug Metab. 2008 Sep;9(7):668-78. Review. PubMed PMID: 18781917.

10: Dashwood RH, Ho E. Dietary agents as histone deacetylase inhibitors: sulforaphane and structurally related isothiocyanates. Nutr Rev. 2008 Aug;66 Suppl 1:S36-8. doi: 10.1111/j.1753-4887.2008.00065.x. Review. PubMed PMID: 18673487; PubMed Central PMCID: PMC2656672.

11: Clarke JD, Dashwood RH, Ho E. Multi-targeted prevention of cancer by sulforaphane. Cancer Lett. 2008 Oct 8;269(2):291-304. doi: 10.1016/j.canlet.2008.04.018. Epub 2008 May 27. Review. PubMed PMID: 18504070; PubMed Central PMCID: PMC2579766.

12: Zhang Y, Tang L. Discovery and development of sulforaphane as a cancer chemopreventive phytochemical. Acta Pharmacol Sin. 2007 Sep;28(9):1343-54. Review. PubMed PMID: 17723168.

13: Juge N, Mithen RF, Traka M. Molecular basis for chemoprevention by sulforaphane: a comprehensive review. Cell Mol Life Sci. 2007 May;64(9):1105-27. Review. PubMed PMID: 17396224.

14: Fimognari C, Hrelia P. Sulforaphane as a promising molecule for fighting cancer. Mutat Res. 2007 May-Jun;635(2-3):90-104. Epub 2006 Nov 28. Review. PubMed PMID: 17134937.

15: Brigelius-Flohé R, Banning A. Part of the series: from dietary antioxidants to regulators in cellular signaling and gene regulation. Sulforaphane and selenium, partners in adaptive response and prevention of cancer. Free Radic Res. 2006 Aug;40(8):775-87. Review. PubMed PMID: 17015256.

16: Myzak MC, Dashwood RH. Histone deacetylases as targets for dietary cancer preventive agents: lessons learned with butyrate, diallyl disulfide, and sulforaphane. Curr Drug Targets. 2006 Apr;7(4):443-52. Review. PubMed PMID: 16611031.

17: Gamet-Payrastre L. Signaling pathways and intracellular targets of sulforaphane mediating cell cycle arrest and apoptosis. Curr Cancer Drug Targets. 2006 Mar;6(2):135-45. Review. PubMed PMID: 16529543.

18: Myzak MC, Dashwood RH. Chemoprotection by sulforaphane: keep one eye beyond Keap1. Cancer Lett. 2006 Feb 28;233(2):208-18. Review. PubMed PMID: 16520150; PubMed Central PMCID: PMC2276573.

19: Gills JJ, Jeffery EH, Matusheski NV, Moon RC, Lantvit DD, Pezzuto JM. Sulforaphane prevents mouse skin tumorigenesis during the stage of promotion. Cancer Lett. 2006 May 8;236(1):72-9. Epub 2005 Jul 1. Review. PubMed PMID: 15993536.

20: Fahey JW, Talalay P. Antioxidant functions of sulforaphane: a potent inducer of Phase II detoxication enzymes. Food Chem Toxicol. 1999 Sep-Oct;37(9-10):973-9. Review. PubMed PMID: 10541453.  



Additional Information

Sulforaphane exhibits anticancer, antidiabetic, and antimicrobial properties in experimental models. It is obtained from cruciferous vegetables such as broccoli, Brussels sprouts or cabbages. The enzyme myrosinase transforms glucoraphanin, a glucosinolate, into sulforaphane upon damage to the plant (such as from chewing). Young sprouts of broccoli and cauliflower are particularly rich in glucoraphanin. [source: http://en.wikipedia.org/wiki/Sulforaphane]