D-(-)-Pantolactone - ≥99% , CAS No.599-04-2

CAS: 599-04-2 Cat. No.: P122332 Formule: C₆H₁₀O₃ Poids moléculaire: 130.14 Beilstein Registry Number: 24854272 Numéro CE: 209-963-3

GRADE & PURITY ≥99%

Synonyms

AC1149 | D-Pantolactone | PANTOLACTONE, (-)- | UNII-J288D7O0JS | dihydro-3-hydroxy-4,4-dimethyl- 2(3H)-Furanone | D-(?)-Pantolactone | HY-W010396 | PANTOLACTONE [MI] | pantoyl lactone | s6027 | PANTOLACTONE, R-ISOMER | Z1065885480 | bmse000381 | 2(3H)-Fur

Storage

Stocker à 2-8°C, chargé d'argon

Shipped In

Glace humide

Vue d’ensemble

Le D-(-)-Pantolactone est un auxiliaire chiral utilisé dans de nombreuses réactions de synthèse asymétriques.

Elle peut être utilisée comme matière première chirale pour synthétiser :

- une phéromone sexuelle d'insecte appelée 1S,2S,3R-1-acétoxyméthyl-2,3,4,4-tétraméthylcyclopentane.

- (-)-Enantiomère du (R)-8-hydroxy-4,7,7-triméthyl-7,8-dihydrocyclopenta[e]isoindole-1,3(2H,6H)-dione, un alcaloïde norsesquiterpénique.

- Un diterpène bicyclique nommé isofregenedadio

Specifications

Synonymes

AC1149 | D-Pantolactone | PANTOLACTONE, (-)- | UNII-J288D7O0JS | dihydro-3-hydroxy-4,4-dimethyl- 2(3H)-Furanone | D-(?)-Pantolactone | HY-W010396 | PANTOLACTONE [MI] | pantoyl lactone | s6027 | PANTOLACTONE, R-ISOMER | Z1065885480 | bmse000381 | 2(3H)-Fur

Spécifications et pureté

≥99%

Conditions de stockage de stockage

Stocker à 2-8°C, chargé d'argon

Expédié en

Glace humide

Pureté

≥99%

Noms et identifiants

• Pubchem Sid: 508810420
• Sourires canoniques: CC1(COC(=O)C1O)C
• IUPAC Name: (3R)-3-hydroxy-4,4-dimethyloxolan-2-one
• InChIKey: SERHXTVXHNVDKA-BYPYZUCNSA-N
• INCHI: 1S/C6H10O3/c1-6(2)3-9-5(8)4(6)7/h4,7H,3H2,1-2H3/t4-/m0/s1
• Isomères SMILES: CC1(COC(=O)[C@@H]1O)C
• WGK Allemagne: 1
• Poids moléculaire: 130.14
• Beilstein: 24854272
• Reaxy-Rn: 80958
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=80958&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Classe Lactones
      • Subclass Gamma butyrolactones

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Classe: Lactones
• Subclass: Gamma butyrolactones
• Intermediate Tree Nodes: Not available
• Direct Parent: Gamma butyrolactones
• Alternative Parents: Tetrahydrofurans Secondary alcohols Carboxylic acid esters Oxacyclic compounds Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Gamma butyrolactone - Tetrahydrofuran - Secondary alcohol - Carboxylic acid ester - Oxacycle - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Alcohol - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as gamma butyrolactones. These are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
• External Descriptors: butan-4-olide

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mécanismes d'action

Propriétés chimiques et physiques

• Sensibilité: Moisture Sensitive
• Rotation spécifique [α]: [α]25/D −49.8°, c = 2 in H2O
• Point d'ébullition (°C): 120-122°C/15mm
• Point de fusion (°C): 92°C
• Poids moléculaire: 130.139 g/mol
• XLogP3: 0.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 130.063 Da
• Monoisotopic Mass: 130.063 Da
• Topological Polar Surface Area: 46.500 Ų
• Heavy Atom Count: 9
• Formal Charge: 0
• Complexity: 139.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Références

1. Xiao-Jian Zhang, Min Cao, Yi-Fei Luo, Meng-Yu Huang, Fang-Ying Zhu, Zhi-Qiang Liu, Yu-Guo Zheng.  (2023)  Efficient synthesis of D-pantolactone in monophase and organic-aqueous biphase reaction biosystem using a novel conjugated polyketide reductase based on integrated substrate pocket alteration.  BIOCHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.bej.2023.109088]

2. Yaling Huang, Junwen Wan, Min Sun, Tao Feng, Qian Liu, Shiqing Song, Xiaoming Zhang, Chi-Tang Ho.  (2022)  Flavor profile disclosure of Chinese steamed breads (CSBs) by sensomics approach.  Food Bioscience,      [PMID:] [10.1016/j.fbio.2022.102198]

3. Jing Wang, Ruifang Wang, Junyi Wang, Yan Gao, Lina Qiao, Ning Zhang.  (2025)  Recognition of characteristic aroma-active components in Qingke (highand barley) through flavoromics analysis.  FOOD CHEMISTRY,      [PMID:40602137] [10.1016/j.foodchem.2025.145262]

4. Xiaoqian Liu, Fang Yuan, Bei Zhou, Wen Huang, Zhinan Mei, Salam A. Ibrahim, Ying Liu, Xi Feng.  (2025)  Application of GC-O, aroma recombination and omission tests to identify horse urine-like off-odor in Gastrodia elata Blume.  Food Bioscience,      [PMID:] [10.1016/j.fbio.2025.107905]

5. Ken Zheng, Ai-Ping Pang, Fang-Ying Zhu, Yu-Hui Liu, Xiao-Jian Zhang, Qing Yang, Xiang-Yang Li, Jun-ping Zhou, Bo Zhang, Zhi-Qiang Liu, Yu-Guo Zheng.  (2026)  Rational selection of ketopantoate hydroxymethyltransferase with low product feedback inhibition based on binding free energy calculation analysis.  APPLIED AND ENVIRONMENTAL MICROBIOLOGY,      [PMID:42429766] [10.1128/aem.00267-26]