Erucin

4-(methylthio)butyl isothiocyanate Isothiocyanate (ITC)

Function

Erucin is an isothiocyanate phytochemical formed from the glucosinolate glucoerucin, found in cruciferous vegetables such as arugula, broccoli, radish, cabbage, and rocket-family plants. It is structurally related to sulforaphane and participates in similar cellular defense signaling, although its chemical sulfur group differs.

Erucin has been studied for effects on Nrf2-related antioxidant response, phase II detoxification enzymes, inflammatory signaling, vascular biology, and cellular stress adaptation. It can also interconvert with sulforaphane through oxidation-reduction chemistry, linking these compounds within cruciferous vegetable metabolism.

Like other isothiocyanates, erucin is electrophilic and can interact with cysteine residues on regulatory proteins. This property allows it to influence redox-sensitive signaling systems and detoxification responses.

Production

Erucin forms when glucoerucin is hydrolyzed by myrosinase enzyme after cruciferous plant tissue is chopped, chewed, crushed, or otherwise damaged. In intact plants, glucosinolates and myrosinase remain separated until tissue disruption occurs.

Glucoerucin content varies by plant species, cultivar, maturity, growing conditions, sulfur availability, and preparation method. Arugula and rocket-family vegetables are notable sources.

After ingestion, erucin is absorbed and metabolized through glutathione conjugation and the mercapturic acid pathway. It may also undergo metabolic interconversion with sulforaphane depending on redox conditions.

Regulation

Erucin activity is regulated by glucoerucin availability, myrosinase activity, cooking temperature, chewing efficiency, gut microbiome metabolism, absorption, and glutathione conjugation capacity. Preparation methods that preserve myrosinase can increase formation.

Erucin can affect Nrf2 signaling by modifying KEAP1-related regulatory systems and may influence inflammatory pathways such as NF-kB in experimental models. Its biological effects depend on concentration, metabolism, and tissue exposure.

As part of cruciferous vegetable intake, erucin contributes to the broader isothiocyanate network that supports redox signaling, detoxification enzyme expression, and cellular defense adaptation.

Chemical Identity

Molecular Formula: C6H11NS2
Molar Mass: 161.290 g/mol
PubChem CID: 78160

Key Biological Functions

  • Induces phase II enzymes; Nrf2 activation; complementary to sulforaphane.

Key Foods / Plant Sources

Top Foods
  • Arugula (rocket); broccoli; radish
Additional Sources
  • Brassicaceae (Eruca sativa; Brassica spp.).

Bioavailability & Inhibitors

Inhibitor / Factor Effect on Activity / Absorption
Formation depends on myrosinase; enhanced with raw/crushed intake; oil improves absorption.
Note: Factors relate to activation and cellular signaling context. Educational only.

Cellular Pathways Involved

  • Nrf2–ARE; Phase II detox (GST, NQO1).

Low Intake / Context

  • No classical deficiency.

Linked Cancers

  • Detox/anticancer mechanisms (dietary/preclinical)

Linked Ailments / Conditions

  • Inflammation/oxidative stress (diet context)

SUMMARY OF EFFECTS ON THE BODY

  • Immune System: Nrf2/phase II
  • Cardiovascular: redox balance
  • Digestive System: conjugation
  • Skin & Collagen: oxidative defense
  • Cellular Repair: electrophile response

Research

PubChem identity for erucin.