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    Ethyl olivetolate (CAS 38862-65-6,
    𝐶 1 4
    𝐻 2 0
    𝑂 4
    ) is a key aromatic precursor in organic synthesis, primarily used for preparing crystalline Cannabidiol (CBD) and other cannabinoids . It acts as a crucial intermediate, frequently used in condensation reactions to form the cannabinoid backbone, offering a high-yield pathway to CBD and its derivatives.
    Key Uses in Synthesis
    • Cannabinoid Synthesis: Ethyl olivetolate serves as a precursor to cannabidiolic acid and cannabigerolic acid (CBGA) , which are further processed into tetrahydrocannabinol (THC) and CBD.
    • Regioselective Terpenylation: It is used in reactions with terpenoids to construct the meroterpenoid core , a common structure in synthetic cannabinoids.
    • Condensation and Cyclization: It is frequently employed in Lewis acid-catalyzed condensation, particularly with menthadienol or similar terpenoids, to form CBD or its analogs, often with better purification outcomes than using olivetol directly.
    Reaction Characteristics
    • Synthesis Route: Often synthesized by the condensation of methyl hexanoate and dimethyl malonate (or similar precursors), followed by decarboxylation of the ester.
    • Advantages: Compared to using olivetol , ethyl olivetolate provides a defined ester handle that facilitates the regioselective formation of the aromatic-terpenoid bond.
    Key Properties
    • CAS Number: 38862-65-6
    • Linear Formula:
      𝐶 1 4
      𝐻 2 0
      𝑂 4
    • Molecular Weight:
      2 5 2 . 3 1
      g / m o l
    • Appearance: Typically a crystalline solid, making it easier to purify than non-crystalline cannabinoid intermediates.
    • Ethyl Olivetolate | CymitQuimica
      Description:Applications Ethyl Olivetolate is used for preparation of crystalline Cannabidiol for pharmaceutical formulations. Ref...
      CymitQuimica
    • (PDF) A Catalytic, Oxidative Synthesis of Olivetol, Methyl ...
      Mar 15, 2021 — 27. 6. H. SYNOPEN. 2509-9396. Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart. 2021, 5, 86–90. letter. en. 87. SynOpen 20...
      ResearchGate
    • US10981849B1 - Method for preparing cannabinoids
      Thereafter, heptane was added to the mixture, and the product was extracted into the heptane phase. A second extraction using hept...
      Google Patents
    • US 2010/0069651 A1 - Patent Application Publication
      Nov 25, 2009 — The difficulties of the synthesis belie the simplicity of the structure, and are due, at least in part, to the following: (a) the ...
      patentimages.storage.googleapis.com
    • Process for production of delta-9-tetrahydrocannabinol
      A slight exotherm was observed. After stirring at 10 0C for three hours, HPLC analysis showed the reaction was complete by no furt...
      Google Patents
    • Prenylation of olivetolate by a hemp transferase yields ...
      May 8, 1998 — Prenylation of olivetolate by a hemp transferase yields cannabigerolic acid, the precursor of tetrahydrocannabinol * Introduction.
      ScienceDirect.com
    • Method for preparing cannabinoids - Justia Patents
      Apr 20, 2021 — 2. Description of Associated Art * Another early example of cannabidiol synthesis by hydrolysis-decarboxylation of olivetolate has...
      Justia
    • a-1440-9732.pdf
      Mar 16, 2021 — Catalytic dehydrogenation of cyclic enones using palla- dium on carbon was reported to afford phenols with vary- ing degrees of su...
      Thieme Group
    • Ethyl olivetolate | 38862-65-6 - MilliporeSigma
      Ethyl olivetolate; CAS Number: 38862-65-6; Synonyms: ethyl 2,4-dihydroxy-6-pentylbenzoate; Linear Formula: C14H20O4; find ChemScen...
      www.sigmaaldrich.com
    • Buy (E)-oct-4-en-1-ol | 31502-21-3
      Apr 14, 2024 — (E)-oct-4-en-1-ol Flavoring Agent : It is used as a flavoring agent in food products due to its aromatic properties. Chemical Inte...
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    • Figure 1 from Identification of olivetolic acid cyclase from Cannabis sativa reveals a unique catalytic route to plant polyketides
      (A) The pathway leading to the major cannabinoids Δ9-tetrahydrocannabinolic acid (THCA) and cannabidiolic acid (CBDA),whichdecarbo...
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    • CAS 773140-43-5: ethyl 4-aminopyridine-2-carboxylate
      This compound typically appears as a solid or crystalline substance and is soluble in polar organic solvents. Its ( Ethyl 4-aminop...
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    • Ethyl Olivetolate | CymitQuimica
      Description:Applications Ethyl Olivetolate is used for preparation of crystalline Cannabidiol for pharmaceutical formulations. Ref...
      CymitQuimica
    • (PDF) A Catalytic, Oxidative Synthesis of Olivetol, Methyl ...
      Mar 15, 2021 — 27. 6. H. SYNOPEN. 2509-9396. Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart. 2021, 5, 86–90. letter. en. 87. SynOpen 20...
      ResearchGate
    • US10981849B1 - Method for preparing cannabinoids
      Thereafter, heptane was added to the mixture, and the product was extracted into the heptane phase. A second extraction using hept...
      Google Patents
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    38862-65-6 | Ethyl olivetolate


    ChemScene
    https://www.chemscene.com › ... › Phenol
    ChemScene
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    ChemScene Provide CAS 38862-65-6, Ethyl olivetolate , Ethyl 2,4-dihydroxy-6-pentylbenzoate, Formula:C14H20O4, MW:252.3100. We also provide services including ...
    $37.00 · 5.0 (1)

    Ethyl olivetolate | 38862-65-6


    Sigma-Aldrich
    https://www.sigmaaldrich.com › product › chemscenell...
    Sigma-Aldrich
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    Ethyl olivetolate ; Purity. 98% ; Storage temp. 4C, stored under nitrogen ; Country of Origin. CN ; Physical Form. Solid ; Boiling Point. 420.4+-30.0 C at 760 mmHg ... Read more
    Missing: Organic ‎| Show results with: Organic

    Cannabidiol Discovery and Synthesis—a Target‐Oriented ...


    Chemistry Europe
    https://chemistry-europe.onlinelibrary.wiley.com › doi
    Chemistry Europe
    https://chemistry-europe.onlinelibrary.wiley.com › doi
    Aug 11, 2020 — In 1965, the group of Mechoulam carried out the first total synthesis of (±)-2 using citral (20) and olivetol (27) as starting materials. The ... Read more

    Ethyl Olivetolate


    CymitQuimica
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    CymitQuimica
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    Ethyl Olivetolate is used for preparation of crystalline Cannabidiol for pharmaceutical formulations. Read more
    €87.00

    US10981849B1 - Method for preparing cannabinoids


    Google Patents
    https://patents.google.com › patent
    Google Patents
    https://patents.google.com › patent
    This synthesis method was able to achieve a 57.5% yield of cannabidiol over two steps from ethyl olivetolate . Figure US10981849-20210420-C00003. Moreover ... Read more

    US 2010/0069651 A1 - Patent Application Publication


    googleapis.com
    https://patentimages.storage.googleapis.com › ...
    googleapis.com
    https://patentimages.storage.googleapis.com › ...
    PDF
    Nov 25, 2009 — HPLC analysis showed the organic phase to be free of any residual ethyl olivetolate . The heptane phase was concentrated under reduced ... Read more

    Ethyl olivetolate | C14H20O4 | CID 12470331 - PubChem - NIH


    National Institutes of Health (.gov)
    https://pubchem.ncbi.nlm.nih.gov › compound
    National Institutes of Health (.gov)
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    Ethyl olivetolate | C14H20O4 | CID 12470331 - structure, chemical names, physical and chemical properties, classification, patents, literature, ...
    Missing: Organic ‎ Synthesis

    A simple and practical synthesis of olivetol - ACS Publications


    ACS Publications
    https://pubs.acs.org › doi
    ACS Publications
    https://pubs.acs.org › doi
    An improved iodine-catalyzed aromatization reaction and its application in the synthesis of a key intermediate of cannabidiol. Read more

    (PDF) A Catalytic, Oxidative Synthesis of Olivetol, Methyl ...


    ResearchGate
    https://www.researchgate.net › ... › Orthogonalization
    ResearchGate
    https://www.researchgate.net › ... › Orthogonalization
    Mar 15, 2021 — Olivetol, methyl olivetolate and a series of orthogonally protected methyl ether derivatives were synthesized from commonly available precursors. Read more

    Factory Supply Ethyl Olivetolate For Organic Synthesis,Ethyl ...


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    Ethyl Olivetolate (CAS No.38862-65-6​) ​​ is a synthetic organic chemical belonging to the important class of ​alkylresorcinol derivatives.

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