Sclareol

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Sclareol
Sclareol.svg
Names
IUPAC name
Labd-14-ene-8,13-diol
Systematic IUPAC name
(1R,2R,4aS,8aS)-1-[(3R)-3-Hydroxy-3-methylpent-4-en-1-yl]-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C20H36O2/c1-7-18(4,21)13-9-16-19(5)12-8-11-17(2,3)15(19)10-14-20(16,6)22/h7,15-16,21-22H,1,8-14H2,2-6H3/t15-,16+,18-,19-,20+/m0/s1 X mark.svgN
    Key: XVULBTBTFGYVRC-HHUCQEJWSA-N X mark.svgN
  • InChI=1/C20H36O2/c1-7-18(4,21)13-9-16-19(5)12-8-11-17(2,3)15(19)10-14-20(16,6)22/h7,15-16,21-22H,1,8-14H2,2-6H3/t15-,16+,18-,19-,20+/m0/s1
    Key: XVULBTBTFGYVRC-HHUCQEJWBX
  • CC1(C)CCC[C@@]2(C)[C@@]1([H])CC[C@@](C)(O)[C@@H]2CC[C@](O)(C)C=C
Properties
C20H36O2
Molar mass 308.506 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Sclareol is a fragrant chemical compound found in Salvia sclarea , from which it derives its name. [1] It is classified as a bicyclic diterpene alcohol having roles in plant growth, development, defense, and attraction of pollinators. [1] [2]

Contents

It is an amber-colored solid with a sweet, herbaceous, balsamic scent used as a fragrance in perfume manufacturing, and as a flavoring agent. [1] [3] Sclareol is the most common starting material for manufacturing ambroxide (tradenames, Ambrox or Ambroxan), which is used as a fixative in commercial perfumes. [1]

Sclareol is also extracted from the flowers of Cistus creticus , Nicotiana glutinosa , and Cleome spinosa . [1]

Plant synthesis and function

Sclareol is mainly produced in the glandular trichomes of sage flower calyces. [2] It is formed via a methylerythritol-phosphate biosynthetic pathway. [2]

As a diterpene, sclareol is among thousands of natural compounds existing in plants with roles in plant growth, development, and interactions with other organisms, such as attraction of pollinators or defense against pathogens and pests. [1] [2]

Manufacturing

Sclareol is a component of Salvia plants spread widely around the world, particularly in the Mediterranean basin and Western Asia where the plants and sclareol are harvested and exploited for their earthy aromatic properties. [2]

Sclareol is extracted by steam distillation of fresh flowers, then purified by further extraction using an organic solvent. [2] Sclareol is applied in the commercial synthesis of ambroxide. [1] [2]

As of 2021, genetic enhancement of plants producing sclareol was under study for improving yields in fragrance and flavor manufacturing. [2]

References

  1. 1 2 3 4 5 6 7 Caniard A, Zerbe P, Legrand S, Cohade A, Valot N, Magnard JL, Bohlmann J, Legendre L (July 2012). "Discovery and functional characterization of two diterpene synthases for sclareol biosynthesis in Salvia sclarea (L.) and their relevance for perfume manufacture". BMC Plant Biology. 12: 119. doi: 10.1186/1471-2229-12-119 . PMC   3520730 . PMID   22834731.
  2. 1 2 3 4 5 6 7 8 Chalvin C, Drevensek S, Gilard F, et al. (October 2021). "Sclareol and linalyl acetate are produced by glandular trichomes through the MEP pathway". Horticulture Research. 8 (1): 206. doi:10.1038/s41438-021-00640-w. PMC   8484277 . PMID   34593779.
  3. ↑ "Sclareol". PubChem, US National Library of Medicine. 27 September 2025. Retrieved 1 October 2025.
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