Sinigrin (Aliphatic Glucosinolate · AITC Precursor · Antimicrobial · Mustard Pungency)

Compound	Sinigrin
Chemical class	Glucosinolate — Aliphatic (Allyl glucosinolate)
CAS	3952-98-9
Primary source	Brassica nigra (black mustard), Armoracia rusticana (horseradish), Wasabia japonica (wasabi)
Key applications	AITC precursor (pungency), antimicrobial, anti-inflammatory, chemopreventive
Claim strength	Moderate
Typical form	Black mustard extract; horseradish extract; sinigrin isolate; wasabi extract
Buy from Herbuno	Black Mustard Extract Powder - Brassica Nigra | Sarson →

Name origin: From Sinapis (mustard genus, from which black mustard was once classified as Sinapis nigra). Sinigrin is the allyl glucosinolate — the simplest aliphatic glucosinolate, with a three-carbon allyl side chain. It is the primary glucosinolate of black mustard (Brassica nigra), horseradish, and wasabi, and is the precursor to allyl isothiocyanate (AITC) — the pungent compound responsible for mustard heat and wasabi burn. Traditional use: Mustard (Brassica nigra, Sarson in Hindi) has been used as a culinary spice, digestive stimulant, topical counterirritant (mustard plaster), and antimicrobial for over 5,000 years across Indian, Mediterranean, and European traditions. Mustard seeds are one of the oldest documented cultivated spices (referenced in ancient Sanskrit texts). Horseradish and wasabi preparations have traditional antimicrobial use in European and Japanese food preservation and medicine. Research trajectory: Sinigrin and its hydrolysis product AITC have documented antimicrobial, anti-inflammatory, antifungal, and chemopreventive properties. Sinigrin intact has been found to have direct anti-inflammatory activity beyond its role as AITC precursor, including modulation of Wnt/β-catenin signalling in colon cancer cell models. Commercial source: Black Mustard Extract (liquid, powder, oil-soluble formats) from Herbuno. See sourcing options below.

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Evidence for Sinigrin Applications

AITC generation — pungency and antimicrobial: Sinigrin + myrosinase → allyl isothiocyanate (AITC) + glucose + sulfate. AITC is responsible for the characteristic heat of black mustard, horseradish, and wasabi, and has potent broad-spectrum antimicrobial activity. This is the primary commercial application of sinigrin-containing extracts. Claim strength: Moderate.

Anti-inflammatory (direct sinigrin activity): Sinigrin inhibits NF-κB and modulates Wnt/β-catenin signalling in cell models independently of AITC conversion. Anti-inflammatory activity in LPS-stimulated macrophages at concentrations achievable from intact glucosinolate absorption (partial gut microbial conversion). Claim strength: Moderate.

Chemopreventive: Sinigrin has demonstrated antiproliferative activity against colon, bladder, and prostate cancer cell lines via both AITC-dependent and AITC-independent mechanisms. In vivo chemopreventive activity in azoxymethane-induced colorectal cancer animal models. Nrf2 activation via AITC is the primary proposed chemopreventive mechanism. Claim strength: Moderate (preclinical convergent).

Topical counterirritant (traditional): Mustard plaster (sinigrin-containing mustard seed paste applied topically) generates AITC locally, producing warming counterirritant sensation via TRPA1 receptor activation. TRPA1 is the same receptor activated by allicin, cinnamon, and ginger pungent compounds. Historical use for musculoskeletal pain and respiratory congestion (“mustard plaster” chest treatment). Claim strength: Moderate (historical use; TRPA1 mechanism well-characterised).

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Dosage & Formulator Specification

No established human supplement dose for isolated sinigrin. Black mustard preparations: 1–5 g black mustard seed equivalent per day in traditional digestive and antimicrobial contexts. Sinigrin content in black mustard seed: approximately 50–150 mg/g dry seed weight (among the highest glucosinolate densities of any commercial Brassica). For chemopreventive positioning: standardise extract to sinigrin content by HPLC and specify myrosinase status (active or inactive) on CoA. For topical counterirritant applications, sinigrin-containing mustard seed powder at 5–10% in the preparation generates AITC upon addition of water (myrosinase activation).

SAFETY NOTE: Topical application of mustard paste directly to skin can cause significant burns and blistering — TRPA1-mediated irritation at high AITC concentrations. Traditional mustard plasters used cloth barriers. Label topical products clearly with appropriate contact time limitations and burn warnings.

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Frequently Asked Questions — Sinigrin

Is sinigrin the pungent compound in black mustard?
No — sinigrin itself is tasteless. The pungency of black mustard arises when sinigrin is converted to AITC (allyl isothiocyanate) by myrosinase enzyme — which occurs when the seed is crushed or chewed (disrupting the cellular separation between sinigrin and myrosinase). Dry ground mustard is not pungent; adding water activates myrosinase and generates AITC within minutes, producing the characteristic heat. This is why prepared mustard (with water) is more pungent than equal amounts of dry mustard powder alone.

Is wasabi the same as horseradish?
Both are sinigrin-rich plants that generate AITC via myrosinase, producing similar pungent flavour profiles. However, they are botanically different: horseradish is Armoracia rusticana (Brassicaceae family); wasabi is Wasabia japonica (also Brassicaceae). True wasabi is very expensive (slow-growing, difficult to cultivate); most commercial “wasabi” paste is horseradish coloured green. The pungency mechanism is identical, but wasabi has a more volatile, nose-directed pungency (AITC vapour) while horseradish pungency is more palate-directed.

Can sinigrin-rich black mustard extract be used as a natural food preservative?
Yes — AITC generated from sinigrin has GRAS status as a food preservative and flavouring in the US. Black mustard extract or mustard essential oil (rich in AITC) is used in food packaging and preservation systems, including active packaging materials that slowly release AITC vapour. Effective against E. coli, Salmonella, Listeria, and food spoilage moulds at concentrations below sensory threshold in some applications.

Does sinigrin have thyroid-disrupting effects?
AITC (sinigrin hydrolysis product) and goitrin (from progoitrin hydrolysis in some other Brassica species) are potential goitrogens at high intake. Sinigrin-derived AITC has some thyroid peroxidase inhibitory activity but at concentrations much higher than typical dietary or supplement exposures. At standard supplement doses, sinigrin from black mustard extract is not expected to produce clinically significant thyroid effects. Standard advisory language for thyroid disease patients is appropriate at higher doses, consistent with other Brassica glucosinolate supplements.

Related compounds: Glucoraphanin, Allyl Isothiocyanate, Gluconasturtiin, Sulforaphane

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Claim-strength scale – High = multiple human RCTs; Moderate = limited trials or strong preclinical convergence; Emerging = early-stage lab or animal data.

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