Ajoene (Organosulfur Vinyldithiin · Antiplatelet · Antifungal · Anti-Leishmanial)
| Compound | Ajoene (E-ajoene / Z-ajoene) |
| Chemical class | Organosulfur — Vinyldithiin / Thiosulfinate derivative |
| CAS | 92285-61-5 (E); 88919-24-8 (Z) |
| Primary source | Allium sativum (garlic) — formed from allicin rearrangement in oil macerate |
| Key applications | Antiplatelet, antifungal, antiproliferative, antithrombotic, anti-leishmanial |
| Claim strength | Moderate |
| Typical form | Aged oil macerate garlic extract; garlic oil (minor ajoene); ajoene isolate |
| Buy from Herbuno |
Name origin: From Spanish ajo (garlic). Ajoene is formed by the acid/heat-catalysed rearrangement and condensation of allicin — primarily in oil macerates of garlic (garlic oil soaked at room temperature for extended periods), producing both E- and Z-isomers. It is not present in fresh garlic and is distinct from the steam-distillation products (DADS, DATS). Ajoene is specifically formed during the preparation of some garlic oil preparations — explaining why different commercial garlic preparations have different bioactivity profiles. Traditional use: Oil macerates of garlic — the preparation method that produces ajoene — have been used in Caribbean (particularly Venezuelan) folk medicine as an antifungal, antiparasitic, and wound-healing preparation. The specific formation of ajoene in these traditional preparations was not understood until identified in the 1980s. Research trajectory: Ajoene has attracted research for its potent antiplatelet activity (more potent than aspirin in vitro), antifungal efficacy (topically, including clinical trials for tinea pedis), anti-Leishmania activity (South American clinical context), and antiproliferative effects. Clinical trials with ajoene cream for topical fungal infection and for cutaneous leishmaniasis are available, providing some of the more direct clinical evidence for a specific garlic organosulfur compound. Commercial source: Allicin 3% Powder and Garlic Extract Powder from Herbuno provide garlic organosulfur matrix; ajoene as a specific standardised extract is not separately available in the current catalogue. See sourcing options below.
Evidence for Ajoene Applications
Antiplatelet — more potent than aspirin in vitro: Ajoene inhibits platelet aggregation by multiple mechanisms: inhibition of fibrinogen binding to GPIIb/IIIa integrin, thromboxane B2 synthesis inhibition, and elevation of platelet cAMP. In comparative in vitro studies, ajoene inhibits ADP, epinephrine, collagen, and arachidonic acid-induced platelet aggregation with potency exceeding aspirin on a molar basis. The irreversible covalent mechanism (thiol alkylation of platelet membrane proteins) gives sustained activity. Claim strength: Moderate (in vitro; limited human data).
Antifungal — topical clinical trials: Topical ajoene gel (0.4% and 0.6%) was evaluated in Venezuelan randomised clinical trials for tinea pedis and tinea corporis — showing comparable efficacy to terbinafine (pharmaceutical antifungal) at 0.6% concentration over 2 weeks. This represents some of the strongest direct clinical evidence for any individual garlic organosulfur compound in a topical application. Claim strength: Moderate (clinical trial evidence).
Anti-Leishmanial: Venezuelan clinical trials demonstrated ajoene gel efficacy for cutaneous leishmaniasis (caused by Leishmania protozoa, transmitted by sandfly bites). In regions where pharmaceutical options are limited, ajoene represents a practical natural alternative studied in controlled clinical contexts. Claim strength: Moderate (clinical trials in endemic population).
Antiproliferative: Ajoene induces apoptosis in multiple cancer cell lines (leukemia, prostate, bladder) via ceramide accumulation, NF-κB inhibition, and ROS generation. E-ajoene is generally more potent than Z-ajoene for antiproliferative effects. Claim strength: Moderate (preclinical).
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Dosage & Formulator Specification
Topical antifungal (from Venezuelan trials): 0.4–0.6% ajoene gel applied twice daily for 7–14 days. No established oral supplement dose for ajoene — it is primarily a topical active. For oral preparations, aged oil macerate garlic extracts may contain small amounts of ajoene alongside DADS and DATS; ajoene-standardised preparations are not widely commercially available as isolated ingredients. For topical formulations, ajoene in a gel or cream base (0.4–0.6%) represents a clinically validated concentration for antifungal applications.
Frequently Asked Questions — Ajoene
Why is ajoene not in fresh garlic?
Ajoene forms specifically when allicin undergoes acid/heat-catalysed rearrangement in an oil medium over time — a process that occurs in oil macerates (garlic steeped in oil at room temperature) or during cooking with oil. Fresh garlic contains allicin (formed enzymatically upon crushing) but ajoene formation requires the specific chemistry of allicin rearrangement in oil. Steam-distilled garlic oil predominantly contains DADS and DATS (not ajoene). Aged oil macerate preparations (like some commercial “aged garlic in oil” preparations) may contain detectable ajoene.
Is ajoene safer than aspirin as an antiplatelet agent?
Direct clinical comparison is not established — aspirin has a well-characterised long-term safety and efficacy profile from decades of RCTs; ajoene’s clinical data are limited to topical applications and short-term in vitro comparisons. For antiplatelet supplement positioning, ajoene’s in vitro potency is impressive but should not be extrapolated to equivalent clinical efficacy or safety to aspirin without controlled human trials of oral ajoene. Include standard antiplatelet advisory language for combination with anticoagulants and antiplatelet medications.
What is the difference between E-ajoene and Z-ajoene?
E-ajoene and Z-ajoene are geometric isomers (cis/trans configuration of the vinyl double bond). They co-occur in garlic oil macerates, typically with the E-isomer predominating (E:Z ratio approximately 1.5–2:1). E-ajoene is generally more potent for antiproliferative and antiplatelet activity. Some commercial preparations have enriched E-ajoene fractions; standard oil macerate preparations provide the natural mixture.
Can ajoene be formulated in a topical antifungal product?
Yes — this is its most clinically validated application. The Venezuelan trials used a gel vehicle at 0.4–0.6% ajoene with 10 mg/ml EDTA and gentamicin in some preparations. Ajoene can be incorporated into modern cosmeceutical vehicles (hydrogel, emulgel, nanoparticle formulations) at effective concentrations. The challenge is sourcing standardised ajoene isolate — commercial availability as a standardised extract is limited, which constrains commercial formulation. Contact Herbuno for current availability of ajoene-containing garlic preparations.
Related compounds: Diallyl Disulfide, Diallyl Trisulfide, Allicin, Alliin
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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