Sclareol

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]

Sclareol

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
CAS Number	515-03-7 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:9053 N
ChemSpider	143282 N
ECHA InfoCard	100.007.450
KEGG	C09183 N
PubChem CID	163263
UNII	B607NP0Q8Y Y
CompTox Dashboard (EPA)	DTXSID0047111
InChI 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 N Key: XVULBTBTFGYVRC-HHUCQEJWSA-N N 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
SMILES CC1(C)CCC[C@@]2(C)[C@@]1([H])CC[C@@](C)(O)[C@@H]2CC[C@](O)(C)C=C
Properties
Chemical formula	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). N verify (what is YN ?) Infobox references

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]