IT1084200B - Microbiological hydroxylation of patchouli alcohol - to give intermediates for nor-patchouli alcohol synthesis - Google Patents

Microbiological hydroxylation of patchouli alcohol - to give intermediates for nor-patchouli alcohol synthesis

Info

Publication number
IT1084200B
IT1084200B IT2722477A IT2722477A IT1084200B IT 1084200 B IT1084200 B IT 1084200B IT 2722477 A IT2722477 A IT 2722477A IT 2722477 A IT2722477 A IT 2722477A IT 1084200 B IT1084200 B IT 1084200B
Authority
IT
Italy
Prior art keywords
patchouli alcohol
ferm
iii
formula
oxidising
Prior art date
Application number
IT2722477A
Other languages
Italian (it)
Original Assignee
Hoffmann La Roche
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche
Application granted granted Critical
Publication of IT1084200B publication Critical patent/IT1084200B/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P15/00—Preparation of compounds containing at least three condensed carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
    • C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • General Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Microbiology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Hydroxylation of patchoulol of formula (I) comprises fermenting it under aq. aerobic conditions with an oxidising microorganism, pref. a fungus is prepd. by hydroxylating (I) to 10-hydroxypatchoulol (III) and oxidising this to the corresp. carboxylic acid which is then oxidatively decarboxylated. New hydroxypatchoulols are of formula (III) except (V) (where one or two R are OH, and the others are H). Pithomyces chartarum var japonicum (FERM P-3828) and P niger nov. sp. (FERM P-3829) are mew microorganisms. (II) is the main odoriferous component of patchouli oil and can now be readily made from the relatively abundant, odourless (I). The novel diols and triols are intermediates for (II) or analogous cpds.
IT2722477A 1977-08-31 1977-09-02 Microbiological hydroxylation of patchouli alcohol - to give intermediates for nor-patchouli alcohol synthesis IT1084200B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3639776A GB1586859A (en) 1977-08-31 1977-08-31 Process for the preparation of patchoulol derivatives

Publications (1)

Publication Number Publication Date
IT1084200B true IT1084200B (en) 1985-05-25

Family

ID=10387766

Family Applications (1)

Application Number Title Priority Date Filing Date
IT2722477A IT1084200B (en) 1977-08-31 1977-09-02 Microbiological hydroxylation of patchouli alcohol - to give intermediates for nor-patchouli alcohol synthesis

Country Status (7)

Country Link
JP (1) JPS5332195A (en)
BE (1) BE858326A (en)
DE (1) DE2739449A1 (en)
FR (2) FR2381007A1 (en)
GB (1) GB1586859A (en)
IT (1) IT1084200B (en)
NL (1) NL7709693A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0024358A1 (en) * 1978-08-10 1981-03-04 L. Givaudan & Cie Société Anonyme Substituted cyclohexadienes
JPS5593646A (en) * 1978-12-30 1980-07-16 Matsushita Electric Works Ltd Fluorescent lamp
ZA200700473B (en) * 2006-01-16 2009-08-26 Reliance Life Sciences Pvt Ltd Process for increased patchulol content in essential oil of pogostemon cablin

Also Published As

Publication number Publication date
FR2381007A1 (en) 1978-09-15
JPS5332195A (en) 1978-03-27
GB1586859A (en) 1981-03-25
FR2381008B1 (en) 1981-09-04
NL7709693A (en) 1978-03-06
BE858326A (en) 1978-03-01
FR2381007B1 (en) 1980-10-17
FR2381008A1 (en) 1978-09-15
DE2739449A1 (en) 1978-03-23

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