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237817

Sigma-Aldrich

D-(−)-Pantolactone

99%

Synonym(s):

(R)-(−)-α-Hydroxy-β,β-dimethyl-γ-butyrolactone, (R)-(−)-β,β-Dimethyl-α-hydroxy-γ-butyrolactone, (R)-(−)-Pantolactone, Pantoic acid γ-lactone

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About This Item

Empirical Formula (Hill Notation):
C6H10O3
CAS Number:
599-04-2
Molecular Weight:
130.14
Beilstein:
80957
EC Number:
209-963-3
MDL number:
MFCD00005392
UNSPSC Code:
12352005
PubChem Substance ID:
24854272
NACRES:
NA.22
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Quality Level

200

Assay

99%

form

solid

optical activity

[α]25/D −49.8°, c = 2 in H2O

bp

120-122 °C/15 mmHg (lit.)

mp

91 °C (lit.)

functional group

ester
hydroxyl

SMILES string

CC1(C)COC(=O)[C@@H]1O

InChI

1S/C6H10O3/c1-6(2)3-9-5(8)4(6)7/h4,7H,3H2,1-2H3/t4-/m0/s1

InChI key

SERHXTVXHNVDKA-BYPYZUCNSA-N

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Application

D-(-)-Pantolactone is a chiral auxiliary used in many asymmetric synthesis reactions.[1][2]
It can be used as a chiral starting material to synthesize:
  • An insect sex pheromone named 1S,2S,3R-1-acetoxymethyl-2,3,4,4-tetrameth-ylcyclopentane.[3]
  • (-)-Enantiomer of (R)-8-hydroxy-4,7,7-trimethyl-7,8-dihydrocyclopenta[e]isoindole-1,3(2H,6H)-dione, a norsesquiterpene alkaloid.[4]
  • A bicyclic diterpene named isofregenedadiol.[5]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF4655V
WXBF4052V
WXBF2365V
WXBF0861V
WXBF0679V

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Asymmetric diels alder reactions and michael type additions with 6 (R)-3′(R)-Pantolactone-substituted-2H-pyran-3 (6H)-one.
Knol J, et al.
Tetrahedron Letters, 32(50), 7465-7468 (1991)
Total synthesis of isofregenedadiol
Kurhade SE, et al.
Organic Letters, 13(14), 3690-3693 (2011)
Enantiospecific synthesis of sex pheromone of the obscure mealybug from pantolactone via tandem conjugate addition/cyclization
Hajare AK, et al.
Tetrahedron Letters, 51(40), 5291-5293 (2010)
Total synthesis of an anticancer norsesquiterpene alkaloid isolated from the fungus Flammulina velutipes
Kashinath K, et al.
Organic & Biomolecular Chemistry, 12(24), 4098-4103 (2014)
Diastereoface-discriminative metal coordination in asymmetric synthesis: d-pantolactone as practical chiral auxiliary for Lewis acid catalyzed Diels-Alder reactions
Poll T, et al.
Tetrahedron Letters, 26(26), 3095-3098 (1985)
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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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