Lipoxygenase-substrate research
Sigma L1376 explicitly documents linoleic acid as a substrate for measuring lipoxygenase activity. [5]
CHEMICAL PROFILE CAS 60-33-3
Properties, Uses, pKa, Safety,
Comparisons & Suppliers
Linoleic acid is the 9Z,12Z C18 diene, a nonconjugated omega-6 fatty acid. It is distinct from linolenic acids and conjugated-linoleic-acid isomer mixtures. [1]
Identity focus: Specified cis free acid; isomer/composition limits separate. Aqueous pKa values depend on conditions; product assay is a separate measurement.
THE ESSENTIALS
A CH₂ group separates the two cis double bonds: C9=C10 and C12=C13. They are methylene-interrupted, not conjugated. Counting from the methyl end places the first double bond at n-6.
Linoleic acid is the 9Z,12Z C18 diene, a nonconjugated omega-6 fatty acid. It is distinct from linolenic acids and conjugated-linoleic-acid isomer mixtures. [1] [3]
Safety at a glance — TCI L0124 identifies eye irritation and possible long-lasting aquatic harm, with air/light/heat sensitivity and inert-gas refrigerated storage. Sigma specifies −20 °C despite ambient shipment; Wako’s lower-assay product specifies room temperature. Follow the exact product rather than a universal rule, control contact/environmental release, and request oxidation and stability documentation. [4] [5] [6]
Condensed connectivity schematic; see the specified stereochemical identity below. [1]
Sigma L1376 explicitly documents linoleic acid as a substrate for measuring lipoxygenase activity. [5]
Sigma documents preparation of linoleic-acid hydroperoxide samples for oxidation studies. [5]
The supplier section separates package size, assay, grade, and market context for three named products. [4] [5] [6]
GO A LITTLE DEEPER
A CH₂ group separates the two cis double bonds: C9=C10 and C12=C13. They are methylene-interrupted, not conjugated. Counting from the methyl end places the first double bond at n-6. [1]
The methylene between the double bonds is a bis-allylic site relevant to oxidation chemistry. Air/light/heat exposure and oxidation products require product-specific controls. Biological nutrient context is separate from purchasing a free-acid laboratory reagent. [1] [12]
The molecular identity specifies carbon count and double-bond geometry. A salt, ester, oil blend or oxidation product is separately identified. Overall assay, acid equivalents, isomer composition and package measurement basis remain separate specifications. [1] [2] [4] [5] [6]
Acid–base reference values describe equilibria under specified conditions. They are not a substitute for a validated formulation or an assay on the purchased lot.
MAKE THE CONNECTION
Similar names and functional groups do not mean interchangeable chemicals.
SIDE-BY-SIDE COMPARISON
Fixed comparison for this prototype. Acid selectors are disabled; additional comparisons are coming later.
| Property | Linoleic Acid | Oleic Acid |
|---|---|---|
| Molecular formula | C₁₈H₃₂O₂ [1] | C₁₈H₃₄O₂ [7] |
| Molecular weight | 280.4 g/mol [1] | 282.5 g/mol [7] |
| Carbon atoms | 18 [1] | 18 [7] |
| Carboxyl groups | 1 [1] | 1 [7] |
| Structure | HOOC–(CH₂)₇–CH=CH–CH₂–CH=CH–(CH₂)₄–CH₃ · 9Z,12Z [1] | HOOC–(CH₂)₇–CH=CH–(CH₂)₇–CH₃ · 9Z [7] |
| Chemical family | C18 cis,cis nonconjugated polyunsaturated fatty acid [1] | C18 cis monounsaturated fatty acid [7] |
| Identity focus | Specified cis free acid; isomer/composition limits separate [1] | Specified cis free acid; isomer/composition limits separate [7] |
| pKa context | 4.77 (water, 25 °C; IUPAC compilation; ionic strength/method not established) [2] | 5.02 (aqueous solution, 25 °C; Riddick reference; ionic strength/method not established) [11] |
Choose 9Z,12Z linoleic acid for a specified diene or enzyme-substrate method; choose oleic acid for a monoene target. Require position/geometry, oxidation limits and formulation identity before considering a substitution or dietary-grade claim. [1] [3] [7]
Match HOOC–(CH₂)₇–CH=CH–CH₂–CH=CH–(CH₂)₄–CH₃ · 9Z,12Z and the method’s required chemical form.
Match HOOC–(CH₂)₇–CH=CH–(CH₂)₇–CH₃ · 9Z; verify the identity before substituting a related acid.
Before choosing: match the reaction or formulation, then verify the exact form, grade, assay basis, and impurities. These contexts do not establish suitability for an industrial or regulated application.
FROM STRUCTURE TO APPLICATION
Sigma L1376 explicitly documents linoleic acid as a substrate for measuring lipoxygenase activity. This is direct laboratory use with method-specific preparation, not a certified clinical or nutritional product. [5]
Sigma documents preparation of linoleic-acid hydroperoxide samples for oxidation studies. These products are derivatives/oxidation products; the role of the starting free acid is intermediate use. [5]
SOURCE WITH CONTEXT
Compare specific products and package options. Listings are not ranked recommendations.
Package sizes stay grouped under the supplier product. Assay methods, product forms, and regional markets remain visible. TCI 97% GC/titration liquid is packaged by mass, Sigma ≥98% has an unstated method, and Wako 88% capillary-GC material is packaged by volume. Wako’s 88% assay is not aqueous concentration. Sigma’s alpha-linoleic title is checked against CAS and 9Z,12Z structure, not confused with alpha-linolenic acid.
Scroll horizontally if needed. Supplier and package identity stay visible.
| Supplier | Product / Grade | Purity / Assay | Package Size | Public Price | Normalized Price | Documentation | Last Checked | Action |
|---|---|---|---|---|---|---|---|---|
| TCI AmericaLinoleic Acid | Named grade not statedL0124 · 5 gLiquid packaged in ampoules by mass; refrigerated 0–10 °C, inert gas and protection from light/air/heat. | GC: minimum 97.0% Neutralization titration: minimum 97.0% | 5 g | $68.00USD · US public price | Not comparedGrades, assay bases, or forms differ | Document notes: TCI America
| View Product: TCI America, L0124 · 5 g (opens new tab) | |
| Named grade not statedL0124 · 25 gLiquid packaged in ampoules by mass; refrigerated 0–10 °C, inert gas and protection from light/air/heat. | GC: minimum 97.0% Neutralization titration: minimum 97.0% | 25 g | $179.00USD · US public price | Not comparedGrades, assay bases, or forms differ | View Product: TCI America, L0124 · 25 g (opens new tab) | |||
| Sigma-AldrichLinoleic Acid | Named grade not statedL1376-10MGCAS and stereochemical structure specify 9Z,12Z linoleic acid despite “α-Linoleic acid” title; not alpha-linolenic acid. 5 g / 25 g list prices shown; promotional USD 79.13 / 307.70 also displayed. −20 °C storage, ambient shipment. | Minimum 98%; method not stated | 10 mg | $29.00USD · US public list price | Not comparedGrades, assay bases, or forms differ | Document notes: Sigma-Aldrich
| View Product: Sigma-Aldrich, L1376-10MG (opens new tab) | |
| Named grade not statedL1376-500MGCAS and stereochemical structure specify 9Z,12Z linoleic acid despite “α-Linoleic acid” title; not alpha-linolenic acid. 5 g / 25 g list prices shown; promotional USD 79.13 / 307.70 also displayed. −20 °C storage, ambient shipment. | Minimum 98%; method not stated | 500 mg | $54.60USD · US public list price | Not comparedGrades, assay bases, or forms differ | View Product: Sigma-Aldrich, L1376-500MG (opens new tab) | |||
| Named grade not statedL1376-1GCAS and stereochemical structure specify 9Z,12Z linoleic acid despite “α-Linoleic acid” title; not alpha-linolenic acid. 5 g / 25 g list prices shown; promotional USD 79.13 / 307.70 also displayed. −20 °C storage, ambient shipment. | Minimum 98%; method not stated | 1 g | $60.10USD · US public list price | Not comparedGrades, assay bases, or forms differ | View Product: Sigma-Aldrich, L1376-1G (opens new tab) | |||
| Named grade not statedL1376-5GCAS and stereochemical structure specify 9Z,12Z linoleic acid despite “α-Linoleic acid” title; not alpha-linolenic acid. 5 g / 25 g list prices shown; promotional USD 79.13 / 307.70 also displayed. −20 °C storage, ambient shipment. | Minimum 98%; method not stated | 5 g | $93.10USD · US public list price | Not comparedGrades, assay bases, or forms differ | View Product: Sigma-Aldrich, L1376-5G (opens new tab) | |||
| Named grade not statedL1376-10GCAS and stereochemical structure specify 9Z,12Z linoleic acid despite “α-Linoleic acid” title; not alpha-linolenic acid. 5 g / 25 g list prices shown; promotional USD 79.13 / 307.70 also displayed. −20 °C storage, ambient shipment. | Minimum 98%; method not stated | 10 g | $178.00USD · US public list price | Not comparedGrades, assay bases, or forms differ | View Product: Sigma-Aldrich, L1376-10G (opens new tab) | |||
| Named grade not statedL1376-25GCAS and stereochemical structure specify 9Z,12Z linoleic acid despite “α-Linoleic acid” title; not alpha-linolenic acid. 5 g / 25 g list prices shown; promotional USD 79.13 / 307.70 also displayed. −20 °C storage, ambient shipment. | Minimum 98%; method not stated | 25 g | $362.00USD · US public list price | Not comparedGrades, assay bases, or forms differ | View Product: Sigma-Aldrich, L1376-25G (opens new tab) | |||
| FUJIFILM WakoLinoleic Acid | Wako 1st Grade126-03612Research / further manufacturing; Japan stock does not confirm US availability. Lower-assay neat liquid product, not an 88% aqueous solution. Volume packages are not normalized against higher-assay mass packages; impurities and isomer composition require lot documentation. | 88.0+% (Capillary GC) | 25 mL | $45.00USD · US catalog list price | Not comparedGrades, assay bases, or forms differ | Document notes: FUJIFILM Wako
| View Product: FUJIFILM Wako, 126-03612 (opens new tab) | |
| Wako 1st Grade128-03611Research / further manufacturing; Japan stock does not confirm US availability. Lower-assay neat liquid product, not an 88% aqueous solution. Volume packages are not normalized against higher-assay mass packages; impurities and isomer composition require lot documentation. | 88.0+% (Capillary GC) | 100 mL | $84.00USD · US catalog list price | Not comparedGrades, assay bases, or forms differ | View Product: FUJIFILM Wako, 128-03611 (opens new tab) | |||
| Wako 1st Grade120-03615Research / further manufacturing; Japan stock does not confirm US availability. Lower-assay neat liquid product, not an 88% aqueous solution. Volume packages are not normalized against higher-assay mass packages; impurities and isomer composition require lot documentation. | 88.0+% (Capillary GC) | 500 mL | $333.00USD · US catalog list price | Not comparedGrades, assay bases, or forms differ | View Product: FUJIFILM Wako, 120-03615 (opens new tab) |
Linoleic Acid
Named grade not stated
Liquid packaged in ampoules by mass; refrigerated 0–10 °C, inert gas and protection from light/air/heat.
Last checked:
Linoleic Acid
Named grade not stated
CAS and stereochemical structure specify 9Z,12Z linoleic acid despite “α-Linoleic acid” title; not alpha-linolenic acid. 5 g / 25 g list prices shown; promotional USD 79.13 / 307.70 also displayed. −20 °C storage, ambient shipment.
Last checked:
Linoleic Acid
Wako 1st Grade
Research / further manufacturing; Japan stock does not confirm US availability. Lower-assay neat liquid product, not an 88% aqueous solution. Volume packages are not normalized against higher-assay mass packages; impurities and isomer composition require lot documentation.
Last checked:
COA = Certificate of Analysis · SDS = Safety Data Sheet · COO = Certificate of Origin.
Lookup means a retrieval option was visible, not that a lot certificate was reviewed. Check supplier means availability or the applicable document was not verified.
Prices may vary by quantity, account, contract, geography, and availability. These products have different grades, assay bases, or forms; no normalized comparison is shown. Foreign-market prices are reference listings only. No currency conversion, mass-to-volume conversion, or ranking is applied. Confirm equivalent specifications and a current quote before comparison. [4] [5] [6]
pKa: CONDITION-DEPENDENT. IUPAC aqueous compilation gives 4.77 at 25 °C; ionic strength/method unestablished. Retained as a compiled reference, not an emulsion/interface constant. Melting point: CONFLICT UNRESOLVED. −5 °C and −6.9 °C sources differ; composition/method cause unestablished. Boiling point: CONDITION-DEPENDENT. 177 °C at 0.5 mmHg and 229–230 °C at 16 mmHg retain their different pressures; no ordinary atmospheric value inferred. Solubility / density: CONDITION-DEPENDENT. Temperature retained; Wako density belongs to the 88% product. No mass/volume normalized price inferred. Stereochemistry / formulation: CONDITION-DEPENDENT. 9Z,12Z identity is verified, while quantitative isomer and oxidation impurity limits remain unverified. No linolenic or CLA-mixture identity substituted.
Only the displayed identity, specification, packages, public prices and stated documentation evidence were reviewed. Current stock, lead times, shipping eligibility, contract pricing, lot certificates, and regulatory suitability are unverified.
There are no paid placements. Future paid listings will show “Sponsored” in both views; payment will not determine chemistry interpretation or imply a ranking.
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FOR YOUR REFERENCE
Identity, product reference properties, and handling context.
Connectivity SMILES describes connectivity; it is not an independent stereochemical assignment. CAS and product-form distinctions are supported by the supplier listings. [1] [4] [5] [6]
Liquid at 20 °C. Product temperatures and composition affect the relevant physical and storage specification; a mass-filled ampoule is not a solid product. [13] [4] [5]
Hydrate, concentration, stereoisomer, and temperature can change the relevant specification. Product reference data are not a reviewed lot certificate.
Reference pKa: 4.77 (water, 25 °C; IUPAC compilation; ionic strength/method not established). [2]
pKa: CONDITION-DEPENDENT. IUPAC aqueous compilation gives 4.77 at 25 °C; ionic strength/method unestablished. Retained as a compiled reference, not an emulsion/interface constant. Melting point: CONFLICT UNRESOLVED. −5 °C and −6.9 °C sources differ; composition/method cause unestablished. Boiling point: CONDITION-DEPENDENT. 177 °C at 0.5 mmHg and 229–230 °C at 16 mmHg retain their different pressures; no ordinary atmospheric value inferred. Solubility / density: CONDITION-DEPENDENT. Temperature retained; Wako density belongs to the 88% product. No mass/volume normalized price inferred. Stereochemistry / formulation: CONDITION-DEPENDENT. 9Z,12Z identity is verified, while quantitative isomer and oxidation impurity limits remain unverified. No linolenic or CLA-mixture identity substituted.
Temperature, ionic strength, and the use of activities versus concentrations matter in quantitative work. These reference values are not buffer recipes.
TCI L0124 identifies eye irritation and possible long-lasting aquatic harm, with air/light/heat sensitivity and inert-gas refrigerated storage. Sigma specifies −20 °C despite ambient shipment; Wako’s lower-assay product specifies room temperature. Follow the exact product rather than a universal rule, control contact/environmental release, and request oxidation and stability documentation. [4] [5] [6]
Hazard classifications can vary by concentration, product, supplier and jurisdiction. Review the SDS for the exact product before handling. This summary does not replace the SDS.
Supplier safety information and SDS retrieval (opens new tab)
A product-page safety classification is not verification of every regional SDS. Confirm product code, chemical form and current local document.
Review supplier documentationCOMMON QUESTIONS
A CH₂ group separates the two cis double bonds: C9=C10 and C12=C13. They are methylene-interrupted, not conjugated. Counting from the methyl end places the first double bond at n-6. [1]
Oleic acid has only the 9Z bond; linoleic acid adds 12Z and loses two more hydrogens. Sorbic acid’s conjugated E,E diene is a different pattern. A diene label alone does not establish interchangeable reactivity or formulation function. [7]
TCI 97% GC/titration liquid is packaged by mass, Sigma ≥98% has an unstated method, and Wako 88% capillary-GC material is packaged by volume. Wako’s 88% assay is not aqueous concentration. Sigma’s alpha-linoleic title is checked against CAS and 9Z,12Z structure, not confused with alpha-linolenic acid. [4]
No. The table retains differing grades, assay bases, forms, and markets. No normalized ranking or currency conversion is applied. [5]
pKa: CONDITION-DEPENDENT. IUPAC aqueous compilation gives 4.77 at 25 °C; ionic strength/method unestablished. Retained as a compiled reference, not an emulsion/interface constant. Melting point: CONFLICT UNRESOLVED. −5 °C and −6.9 °C sources differ; composition/method cause unestablished. Boiling point: CONDITION-DEPENDENT. 177 °C at 0.5 mmHg and 229–230 °C at 16 mmHg retain their different pressures; no ordinary atmospheric value inferred. Solubility / density: CONDITION-DEPENDENT. Temperature retained; Wako density belongs to the 88% product. No mass/volume normalized price inferred. Stereochemistry / formulation: CONDITION-DEPENDENT. 9Z,12Z identity is verified, while quantitative isomer and oxidation impurity limits remain unverified. No linolenic or CLA-mixture identity substituted.
The RFQ is a prototype that prepares an on-screen brief. Nothing is sent to suppliers. Confirm actual bulk terms directly with the supplier.
TRACE THE INFORMATION
Identity and compiled reference values are separated from supplier-specific specifications. Structural comparisons and buyer guidance are editorial interpretation. Sources were checked October 3, 2026; supplier information can change.
Neutral molecular identity verified independently through PUG REST; CAS also checked on all selected supplier products.
The cited reference and available conditions are retained; unspecified measurement conditions are not inferred.
Attributed application records reviewed claim by claim. Free acid, intermediate, derivative and biological context are distinguished.
Direct product checked October 3, 2026. Identity, listed assay methods, packages, market, prices and documentation interfaces inspected. Lot certificates and stock are not verified.
Direct product checked October 3, 2026. Identity, listed assay methods, packages, market, prices and documentation interfaces inspected. Lot certificates and stock are not verified.
Direct product checked October 3, 2026. Identity, listed assay methods, packages, market, prices and documentation interfaces inspected. Lot certificates and stock are not verified.
Primary structural comparison. Practical interpretation does not establish suitability.
Related identity and structural relationship.
Related identity and structural relationship.
Related identity and structural relationship.
Only independently reviewed values are promoted into the comparison; no condition-free acidity ranking.
General carboxylate resonance, acidity and structural interpretation; not authority for this acid’s quantitative constants.
Attributed conditions reviewed; derivative contamination and unresolved discrepancies excluded from unqualified constants.
pKa: CONDITION-DEPENDENT. IUPAC aqueous compilation gives 4.77 at 25 °C; ionic strength/method unestablished. Retained as a compiled reference, not an emulsion/interface constant. Melting point: CONFLICT UNRESOLVED. −5 °C and −6.9 °C sources differ; composition/method cause unestablished. Boiling point: CONDITION-DEPENDENT. 177 °C at 0.5 mmHg and 229–230 °C at 16 mmHg retain their different pressures; no ordinary atmospheric value inferred. Solubility / density: CONDITION-DEPENDENT. Temperature retained; Wako density belongs to the 88% product. No mass/volume normalized price inferred. Stereochemistry / formulation: CONDITION-DEPENDENT. 9Z,12Z identity is verified, while quantitative isomer and oxidation impurity limits remain unverified. No linolenic or CLA-mixture identity substituted.
This informational prototype is not a supplier, quotation service, or endorsement of a product’s fitness for an application. Buyers should verify the applicable specification, certification, and regulatory requirements for their intended use.