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74437

(+)-Nootkatone

≥99.0% (GC)

Synonym(s):

(4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-2(3H)-naphthalenone

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Size/SKUAvailabilityPrice
1 g
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$175.00
2.5 g
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$419.00
$314.25

About This Item

Empirical Formula (Hill Notation):
C15H22O
CAS Number:
Molecular Weight:
218.33
UNSPSC Code:
12352205
NACRES:
NA.22
PubChem Substance ID:
EC Number:
225-124-4
Beilstein/REAXYS Number:
4676969
MDL number:
Assay:
≥99.0% (GC)
Form:
crystals

$175.00


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Quality Segment

assay

≥99.0% (GC)

form

crystals

optical activity

[α]20/D +182.0±5.0°, c = 1% in ethanol

storage condition

under inert gas (Argon)

mp

35-39 °C

functional group

ketone

storage temp.

2-8°C

SMILES string

C[C@@H]1CC(=O)C=C2CC[C@H](C[C@@]12C)C(C)=C

InChI

1S/C15H22O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h8,11-12H,1,5-7,9H2,2-4H3/t11-,12-,15+/m1/s1

InChI key

WTOYNNBCKUYIKC-JMSVASOKSA-N

General description

(+)-nootkatone, a bicyclic conjugated sesquiterpene ketone with a grapefruit-like flavor, is commonly used in fragrance, food, cosmetics and pharmaceutical industry. It can be synthesized from (+)-valencene via biotransformation.[1] (+)-nootkatone is the active ingredient responsible for the antiplatelet effect of Cyperus rotundus, a well-known oriental traditional medicine.[2] It also shows promising efficacy against Staphylococcus aureus biofilms.

Application

(+)-Nootkatone can be used:
  • In the iron(III) porphyrin catalyzed alkene aziridination reaction with organic azides under photo-irradiation condition.
  • As a substrate to synthesize its corresponding triene derivative through reduction-elimination reaction using iridium catalyst.

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This Item
W31662075056218324
assay

≥99.0% (GC)

assay

≥98%

assay

≥70%

assay

97%

Quality Level

100

Quality Level

300

Quality Level

100

Quality Level

100

form

crystals

form

-

form

liquid

form

liquid

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

mp

35-39 °C

mp

-

mp

-

mp

-

optical activity

[α]20/D +182.0±5.0°, c = 1% in ethanol

optical activity

-

optical activity

[α]20/D +100±25°, neat

optical activity

-


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pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Skin Sens. 1

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)



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Questions

1–2 of 2 Questions  
  1. What is the source of this product, is it synthetic or natural 74437 Sigma-Aldrich Nootkatone

    1 answer
    1. This product is typically of synthetic origin. However, source information can be located on the lot-specific Certificate of Origin.

      Helpful?

  2. What is the source of the this product, is it natural or synthetic?

    1 answer
    1. This product is typically of synthetic origin. The source information is listed on the lot-specific Certificate of Origin. Please navigate to the ‘DOCUMENTATION’ section of the Product Detail Page to access a Certificate under the ‘Certificate of Origin’ tab:
      https://www.sigmaaldrich.com/product/aldrich/74437#product-documentation

      Helpful?

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